Phenylpyridine compound and fungicidal compostion containing the same

ABSTRACT

A phenylpyridine compound represented by the formula has an excellent controlling activity against plant diseases:  
                 
 
[, wherein, in the formula, R 1 , R 2 , R 3 , R 4  and R 5  independently represent a hydrogen atom, a halogen atom and the like; R 6  represents a hydrogen atom or a C1-C3 alkyl group; R 7 , R 8  and R 11  independently represent a hydrogen atom, a halogen atom and the like; R 9  and R 10  independently represent a hydroxyl group and the like; W 1 —W 2 ═W 3 —W 4  represents N—CH═CH—CH and the like; X represents an oxygen atom and the like; and Q represents a (C1-C6 alkoxy)methylene and the like].

TECHNICAL FIELD

The present invention relates a phenylpyridine compound and a fungicidalcomposition comprising the same.

BACKGROUND ART

Various compounds having controlling activity against plant diseases areconventionally developed and provided in practical use as an activeingredient of the fungicidal composition, however sometimes theircontrolling activity are not always enough.

DISCLOSURE OF THE INVENTION

The inventor(s) of the present invention, after intensively studying,has found that a phenylpyridine compound (1) represented by thefollowing formula has an excellent controlling activity against plantdiseases and accomplished the present invention.

The present invention provides:

-   [Invention 1] a phenylpyridine compound (1)-   [, wherein, in the formula, R¹, R², R³, R⁴ and R⁵ independently    represent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a    C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl    group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C1-C6    alkoxy group, a C1-C6 haloalkoxy group, a C3-C6 alkenyloxy group, a    C3-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group, a C3-C6    haloalkynyloxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthio    group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkoxy group or a    cyano group; both of R² and R³ may be combined to represent a    trimethylene, a tetramethylene or —CH═CH—CH═CH—;-   R⁶ represents a hydrogen atom or a C1-C3 alkyl group; R⁷, R⁸ and R¹¹    independently represent a hydrogen atom, a halogen atom or a C1-C3    alkyl group;-   R⁹ and R¹⁰ independently represent a hydroxyl group, a halogen atom,    a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group,    a C2-C6 haloalkenyl group, aC2-C6 alkynyl group, aC2-C6 haloalkynyl    group, a C2-C6 cyanoalkyl group, a C1-C6 alkoxy group, a C1-C6    haloalkoxy group, a C3-C6 alkenyloxy group, a C3-C6 haloalkenyloxy    group, a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group, a    C2-C6 cyanoalkyloxy group, a C1-C6 alkylthio group, a C1-C6    haloalkylthio group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkoxy    group, a nitro group, a benzyl group or a cyano group; W¹—W²=W³—W⁴    represents N—CR²¹═CR²²—CR²³, CR²⁴—N═CR²⁵—CR²⁶, CR²⁷—CR²⁸═N—CR²⁹ or    CR³⁰—CR³¹═CR³²—N    -   {in which R²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷, R²⁸, R²⁹, R³⁰, R³¹        and R³² independently represent a hydrogen atom, a halogen atom,        a C1-C3 alkyl group, a C1-C3 alkoxy group, a C1-C3 haloalkyl        group};-   X represents an oxygen atom or a sulfur atom;-   Q represents a group illustrated by the following formulas of Q1 or    Q2    -   {in which R¹⁴ represents a hydrogen atom or a C1-C3 alkyl group,        R¹⁵ represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6        haloalkyl group, a C3-C6 alkenyl group, a C3-C6 haloalkenyl        group, a C3-C6 alkynyl group, a C3-C6 haloalkynyl group, a C3-C6        cycloalkyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6        haloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a        (C1-C6 haloalkoxy) carbonyl group, a (C3-C6 alkenyloxy) carbonyl        group, a (C3-C6 haloalkenyloxy)carbonyl group, a (C3-C6        alkynyloxy)carbonyl group, a (C3-C6 haloalkynyloxy)carbonyl        group or a C1-C3 alkylsulfonyl group,    -   Z¹ represents an oxygen atom or a sulfur atom,    -   Z² represents an oxygen atom, NOR¹⁶ (in which R¹⁶ represents a        hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a        C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynyl        group, a C3-C6 haloalkynyl group or a C3-C6 cycloalkyl group),        CR¹⁷R¹⁸ (in which R¹⁷ represents a halogen atom, a C1-C6 alkyl        group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, a C1-C6        haloalkoxy group, a C3-C6 alkenyloxy group, a C3-C6        haloalkenyloxy group, a C3-C6 alkynyloxy group, a C3-C6        haloalkynyloxy group or a C3-C6 cycloalkyloxy group and R¹⁸        represents a hydrogen atom, a halogen atom, a C1-C6 alkyl group        or a C1-C6 haloalkyl group) or NNR¹⁹R²⁰ (in which R¹⁹ and R²⁰        independently represent a hydrogen atom, a C1-C6 alkyl group, a        C1-C6 haloalkyl group, a C3-C6 alkenyl group, a C3-C6        haloalkenyl group, a C3-C6 alkynyl group or a C3-C6 cycloalkyl        group)}];-   (referred to as “the compound of the present invention”    hereinafter.);-   [Invention 2] the phenylpyridine compound (1) according to Invention    1, wherein X is an oxygen atom;-   [Invention 3] the phenylpyridine compound (1) according to any one    of Invention 1 or 2, wherein R⁶ is a hydrogen atom;-   [Invention 4] the phenylpyridine compound (1) according to any one    of Invention 1 to 3, wherein Q is Q¹, R¹⁴ is a hydrogen atom and Z¹    is an oxygen atom;-   [Invention 5] the phenylpyridine compound (1) according to Invention    4, wherein R¹⁵ is a hydrogen atom, a C1-C6 alkyl group, a C1-C6    haloalkyl group, a C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a    C3-C6 alkynyl group, a C3-C6 haloalkynyl group or a C3-C6 cycloalkyl    group;-   [Invention 6] the phenylpyridine compound (1) according to any one    of Invention 1 to 3, wherein Q is Q2 and Z² is NOR¹⁶ (in which R¹⁶    is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a    C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynyl    group, a C3-C6 haloalkynyl group or a C3-C6 cycloalkyl group);-   [Invention 7] the phenylpyridine compound (1) according to any one    of Invention 1 to 6, wherein R¹, R⁴ and R⁵ are hydrogen atoms;-   [Invention 8] the phenylpyridine compound (1) according to any one    of Invention 1 to 6, wherein R¹, R⁴ and R⁵ are hydrogen atoms and R²    is a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C2-C6    alkenyl group, a C3-C6 alkynyl group, a C1-C6 alkoxy group, a C3-C6    alkenyloxy group, a C3-C6 alkynyloxy group, a C1-C6 alkylthio group,    a C3-C6 cycloalkyl group, a C3-C6 cycloalkoxy group or a cyano    group;-   [Invention 9] the phenylpyridine compound (1) according to any one    of Invention 1 to 6, wherein R¹, R², R⁴ and R⁵ are hydrogen atoms;-   [Invention 10] the phenylpyridine compound (1) according to any one    of Invention 1 to 9, wherein each of R⁹ and R¹⁰ is a C1-C6 alkoxy    group, a C1-C6 haloalkoxy group, a C3-C6 alkenyloxy group, a C3-C6    haloalkenyloxy group, a C3-C6 alkynyloxy group, a C3-C6    haloalkynyloxy group, a C2-C6 cyanoalkyloxy group or a C3-C6    cycloalkoxy group;-   [Invention 11] the phenylpyridine compound (1) according to any one    of Invention 1 to 9, wherein each of R⁹ and R¹⁰ is a C1-C4 alkoxy    group;-   [Invention 12] the phenylpyridine compound (1) according to any one    of Invention 1 to 9, wherein R⁹ and R¹⁰ are methoxy groups;-   [Invention 13] the phenylpyridine compound (1) according to any one    of Invention 1 to 12, wherein R⁷, R⁸ and R¹¹ are hydrogen atoms;-   [Invention 14] the phenylpyridine compound (1) according to any one    of claim 1 to 13, wherein W¹—W²═W³—W⁴ is N—CH═CH—CH, CH—N═CH—CH,    CH—CH═N—CH or CH—CH═CH—N;-   [Invention 15] a fungicidal composition comprising the    phenylpyridine compound (1) according to any one of Invention 1 to    14 and a carrier; and-   [Invention 16] a method for controlling plant diseases comprising    applying of the phenylpyridine compound (1) according to any one of    Invention 1 to 14 for plants or soils.

In the representation of R¹, R², R³, R⁴ and R⁵, the halogen atomincludes a fluorine atom, a chlorine atom, a bromine atom and the like;

-   the C1-C6 alkyl group includes a methyl group, an ethyl group, a    propyl group, an isopropyl group, a butyl group, an isobutyl group,    a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl    group, a hexyl group and the like;-   the C1-C6 haloalkyl group includes a fluoromethyl group, a    difluoromethyl group, a trifluoromethyl group, a    chlorodifluoromethyl group, a chlorofluoromethyl group, a    bromodifluoromethyl group, a trichloromethyl group, a    dichlorobromomethyl group, a pentafluoroethyl group, a    2,2,2-trifluoroethyl group, a 1,1-difluoroethyl group, a    2,2-difluoroethyl group, a 2-fluoroethyl group, a    6,6,6-trifluorohexyl group and the like;-   the C2-C6 alkenyl group includes a vinyl group, a 1-propenyl group,    a 2-propenyl group, a 1-methyl-1-propenyl group, a    1-methyl-2-propenyl group, a 2-methyl-1-propenyl group, a    2-methyl-2-propenyl group, a 1-butenyl group, a 2-butenyl group, a    3-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 5-hexenyl    group and the like;-   the C2-C6 haloalkenyl group includes a 1-chlorovinyl group, a    2-chlorovinyl group, a 2,2-dichlorovinyl group, a 2,2-difluorovinyl    group, a 1,2-dichlorovinyl group, a 3,3-dichloro-2-propenyl group, a    3,3-difluoro-2-propenyl group and the like;-   the C2-C6 alkynyl group includes an ethynyl group, a 2-propynyl    group, a 3-butynyl group, a 3-hexynyl group, a 5-hexynyl group and    the like;-   the C2-C6 haloalkynyl group includes a 2-chloroethynyl group, a    2-bromoethynyl group, a 3-chloro-2-propynyl group, a    3-bromo-2-propynyl group, a 6-chloro-5-hexynyl group and the like;    the C1-C6 alkoxy group includes a methoxy group, an ethoxy group, a    propoxy group, an isopropoxy group, a butoxy group, an isobutoxy    group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group,    an isopentyloxy group, a hexyloxy group and the like;-   the C1-C6 haloalkoxy group includes a trifluoromethoxy group, a    difluoromethoxy group, a bromodifluoromethoxy group, a    chlorodifluoromethoxy group, a fluoromethoxy group, a    2,2,2-trifluoroethoxy group, a 1, 1,2,2-tetrafluoroethoxy group, a    5-chloropentyloxy group, a 4-fluoroisopentyloxy group, a    2,2-dichlorohexyloxy group and the like;-   the C3-C6 alkenyloxy group includes a 2-propenyloxy group, a    1-methyl-2-propenyloxy group, a 2-methyl-2-propenyloxy group, a    2-butenyloxy group, a 3-butenyloxy group, a 2-hexenyloxy group, a    5-hexenyloxy group and the like;-   the C3-C6 haloalkenyloxy group includes a 3,3-dichloro-2-propenyloxy    group, a 3,3-difluoro-2-propenyloxy group, a    3,3-dibromo-2-propenyloxy group, a 2,3-dichloropropenyloxy group, a    6-fluoro-2-hexenyloxy group, a 2,2-dichloro-5-hexenyloxy group and    the like;-   the C3-C6 alkynyloxy group includes a 2-propynyloxy group, a    1-methyl-2-propynyloxy group, a 2-butynyloxy group, a 3-butynyloxy    group, a 2-hexynyloxy group, a 5-hexynyloxy group and the like;-   the C3-C6 haloalkynyloxy group includes a 3-chloro-2-propynyloxy    group, a 3-bromo-2-propynyloxy group, a 3-iodo-2-propynyloxy group,    a 6-chloro-5-hexynyloxy group and the like;-   the C1-C6 alkylthio group includes a methylthio group, an ethylthio    group, a propylthio group, an isopropylthio group, a butylthio    group, an isobutylthio group, a sec-butylthio group, a    tert-butylthio group, a pentylthio group, an isopentylthio group, a    hexylthio group and the like;-   the C1-C6 haloalkylthio group includes a trifluoromethylthio group,    a difluoromethylthio group, a bromodifluoromethylthio group, a    chlorodifluoromethylthio group, a fluoromethylthio group, a    2,2,2-trifluoroethylthio group, a 1,1,2,2-tetrafluoroethylthio    group, a 5-chloropentylthio group, a 4-fluoroisopentylthio group, a    2,2-dichlorohexylthio group and the like;-   the C3-C6 cycloalkyl group includes a cyclopropyl group, a    cyclopentyl group, a cyclohexyl group and the like; and-   the C3-C6 cycloalkoxy group includes a cyclopropoxy group, a    cyclopentyloxy group, a cyclohexyloxy group and the like.

In the representation of R⁶, the C1-C3 alkyl group includes a methylgroup, an ethyl group, a propyl group and the like.

In the representation of R⁷, R⁸ and R¹¹, the halogen atom includes afluorine atom, a chlorine atom, a bromine atom and the like.

the C1-C3 alkyl group includes a methyl group, an ethyl group, a propylgroup and the like.

In the representation of R⁹ and R¹⁰, the halogen atom includes afluorine atom, a chlorine atom, a bromine atom and the like;

-   the C1-C6 alkyl group includes a methyl group, an ethyl group, a    propyl group, an isopropyl group, a butyl group, an isobutyl group,    a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl    group, a hexyl group and the like;-   the C1-C6 haloalkyl group includes a fluoromethyl group, a    difluoromethyl group, a trifluoromethyl group, a    chlorodifluoromethyl group, a chlorofluoromethyl group, a    bromodifluoromethyl group, a trichloromethyl group, a    dichlorobromomethyl group, a pentafluoroethyl group, a    2,2,2-trifluoroethyl group, a 2,2-difluoroethyl group, a    2-fluoroethyl group, a 6,6,6-trifluorohexyl group and the like;-   the C2-C6 alkenyl group includes a vinyl group, a 1-propenyl group,    a 2-propenyl group, a 1-methyl-1-propenyl group, a    1-methyl-2-propenyl group, a 2-methyl-1-propenyl group, a    2-methyl-2-propenyl group, a 1-butenyl group, a 2-butenyl group, a    3-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 5-hexenyl    group and the like;-   the C2-C6 haloalkenyl group includes a 1-chlorovinyl group, a    2-chlorovinyl group, a 2,2-dichlorovinyl group, a 2,2-difluorovinyl    group, a 1,2-dichlorovinyl group, a 3,3-dichloropropenyl group, a    3,3-difluoropropenyl group and the like;-   the C2-C6 alkynyl group includes an ethynyl group, a 2-propynyl    group, a 3-butynyl group, a 5-hexynyl group and the like;-   the C2-C6 haloalkynyl group includes a 2-chloroethynyl group, a    2-bromoethynyl group, and a 6-chloro-5-hexynyl group and the like;-   the C2-C6 cyanoalkyl group includes a cyanomethyl group, a    1-cyanoethyl group, a 2-cyanoethyl group and the like;-   the C1-C6 alkoxy group includes a methoxy group, an ethoxy group, a    propoxy group, an isopropoxy group, a butoxy group, an isobutoxy    group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group,    an isopentyloxy group, a hexyloxy group and the like;-   the C1-C6 haloalkoxy group includes a trifluoromethoxy group, a    difluoromethoxy group, a bromodifluoromethoxy group, a    chlorodifluoromethoxy group, a fluoromethoxy group, a    2,2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group, a    5-chloropentyloxy group, a 4-fluoroisopentyloxy group, a    2,2-dichlorohexyloxy group and the like;-   the C3-C6 alkenyloxy group includes a 2-propenyloxy group, a    1-methyl-2-propenyloxy group, a 2-methyl-2-propenyloxy group, a    2-butenyloxy group, a 3-butenyloxy group, a 2-hexenyloxy group, a    5-hexenyloxy group and the like;-   the C3-C6 haloalkenyloxy group includes a 3-chloro-2-propynyloxy    group, a 3-bromo-2-propynyloxy group, a 3-iodo-2-propynyloxy group,    a 6-chloro-5-hexenyloxy group and the like;-   the C3-C6 alkynyloxy group includes a 2-propynyloxy group, a    1-methyl-2-propynyloxy group, a 2-butynyloxy group, a 3-butynyloxy    group, a 2-hexynyloxy group, a 5-hexynyloxy group and the like;-   the C3-C6 haloalkynyloxy group includes a 3-chloro-2-propynyloxy    group, a 3-bromo-2-propynyloxy group, a3-iodo-2-propynyloxy group, a    6-chloro-5-hexynyloxy group and the like;-   the C2-C6 cyanoalkyloxy group includes a cyanomethyloxy group, a    1-cyanoethyloxy group, a 2-cyanoethyloxy group and the like;-   the C1-C6 alkylthio group includes a methylthio group, an ethylthio    group, a propylthio group, an isopropylthio group, a butylthio    group, an isobutylthio group, a sec-butylthio group, a    tert-butylthio group, a pentylthio group, an isopentylthio group, a    hexylthio group and the like;-   the C1-C6 haloalkylthio group includes a trifluoromethylthio group,    a difluoromethylthio group, a bromodifluoromethylthio group, a    chlorodifluoromethylthio group, a fluoromethylthio group, a    2,2,2-trifluoroethylthio group, a 1,1,2,2-tetrafluoroethylthio    group, a 5-chloropentylthio group, a 4-fluoroisopentylthio group, a    2,2-dichlorohexylthio group and the like;-   the C3-C6 cycloalkyl group includes a cyclopropyl group, a    cyclopentyl group, a cyclohexyl group and the like; and-   the C3-C6 cycloalkyloxy group includes a cyclopropyloxy group, a    cyclopentyloxy group, a cyclohexyloxy group and the like.

In the representation of R²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R², R²⁸, R²⁹,R³⁰, R³¹ and R³², the halogen atom includes a fluorine atom, a chlorineatom, a bromine atom and the like;

-   the C1-C3 alkyl group includes a methyl group, an ethyl group, a    propyl group and the like;-   the C1-C3 alkoxy group includes a methoxy group, an ethoxy group, a    propoxy group and the like; and-   the C1-C3 haloalkyl group includes a fluoromethyl group, a    difluoromethyl group, a trifluoromethyl group, a chloromethyl group,    a bromomethyl group, a 2,2,2-trifluoroethyl group, a trichloromethyl    group and the like.

In the representation of R¹⁴, the C1-C3 alkyl group includes a methylgroup, an ethyl group, a propyl group and the like.

In the representation of R¹⁵, the C1-C6 alkyl group includes a methylgroup, an ethyl group, a propyl group, an isopropyl group, a butylgroup, an isobutyl group, a sec-butyl group, a tert-butyl group, apentyl group, an isopentyl group, a hexyl group and the like;

-   the C1-C6 haloalkyl group includes a fluoromethyl group, a    difluoromethyl group, a trifluoromethyl group, a trichloromethyl    group, a chlorofluoromethyl group, a bromodifluoromethyl group, a    2-fluoroethyl group, a 2,2-difluoroethyl group, a    2,2,2-trifluoroethyl group, a 6,6,6-trifluorohexyl group and the    like;-   the C3-C6 alkenyl group includes a 2-propenyl group, a    1-methyl-2-propenyl group, a 1,1-dimethyl-2-propenyl group, a    2-methyl-2-propenyl group, a 2-butenyl group, a 3-butenyl group, a    2-hexenyl group, a 5-hexenyl group and the like;-   the C3-C6 haloalkenyl group includes a 3,3-dichloro-2-propenyl    group, a 2,3-dichloro-2-propenyl group, a 3,3-difluoro-2-propenyl    group and the like;-   the C3-C6 alkynyl group includes a 2-propynyl group, a    1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a    2-butynyl group, a 3-butynyl group, a 2-hexynyl group, a 5-hexynyl    group and the like;-   C3-C6 haloalkynyl group includes a 3-chloro-2-propynyl group, a    3-bromo-2-propynyl group, a 6-chloro-5-hexynyl group and the like;-   the C3-C6 cycloalkyl group includes a cyclopropyl group, a    cyclopentyl group, a cyclohexyl group and the like;-   the (C1-C6 alkyl)carbonyl group includes an acetyl group, an    ethylcarbonyl group, a propylcarbonyl group, an isopropylcarbonyl    group, a butylcarbonyl group, a isobutylcarbonyl group, a    sec-butylcarbonyl group, a tert-butylcarbonyl group, a    pentylcarbonyl group, an isopentylcarbonyl group, a hexylcarbonyl    group and the like;-   the (C1-C6 haloalkyl)carbonyl group includes a chloroacetyl group, a    bromoacetyl group, a difluoroacetyl group, a trifluoroacetyl group,    a trichloroacetyl group, a chlorofluoroacetyl group, a    bromodifluoroacetyl group, a 2-fluoroethylcarbonyl group, a    2,2-difluoroethylcarbonyl group, a 2,2,2-trifluoroethylcarbonyl    group, a 6,6,6-trifluorohexylcarbonyl group and the like;-   the (C1-C6 alkoxy) carbonyl group includes a methoxycarbonyl group,    an ethoxycarbonyl group, a propoxycarbonyl group, an    isopropoxycarbonyl group, a butoxycarbonyl group, an    isobutoxycarbonyl group, a sec-butoxycarbonyl group, a    tert-butoxycarbonyl group, a pentyloxycarbonyl group, an    isopentyloxycarbonyl group, a hexyloxycarbonyl group and the like;-   the (C1-C6 haloalkoxy)carbonyl group includes a    2,2,2-trifluoroethoxycarbonyl group, a    1,1,2,2-tetrafluoroethoxycarbonyl group, a 5-chloropentyloxycarbonyl    group, a 2,2-dichlorohexyloxycarbonyl group and the like;-   the (C3-C6 alkenyloxy)carbonyl group includes a    2-propenyloxycarbonyl group, a 1-methyl-2-propenyloxycarbonyl group,    a 2-methyl-2-propenyloxycarbonyl group, a 2-butenyloxycarbonyl    group, a 3-butenyloxycarbonyl group, a 2-hexenyloxycarbonyl group, a    5-hexenyloxy group carbonyl and the like;-   the (C3-C6 haloalkenyloxy)carbonyl group includes a    3-chloro-2-propynyloxycarbonyl group, a    3-bromo-2-propynyloxycarbonyl group, a 3-iodo-2-propynyloxycarbonyl    group, a 6-chloro-5-hexenyloxycarbonyl group and the like;-   the (C3-C6 alkynyloxy)carbonyl group includes a    2-propynyloxycarbonyl group, a 1-methyl-2-propynyloxycarbonyl group,    a 2-butynyloxycarbonyl group, a 3-butynyloxycarbonyl group, a    2-hexynyloxycarbonyl group, a 5-hexynyloxycarbonyl group and the    like;-   the (C3-C6 haloalkynyloxy)carbonyl group includes a    3-chloro-2-propynyloxycarbonyl group, a    3-bromo-2-propynyloxycarbonyl group, a 3-iodo-2-propynyloxycarbonyl    group, a 6-chloro-5-hexynyloxycarbonyl group and the like; and-   the C1-C3 alkylsulfonyl group includes a methanesulfonyl group, an    ethanesulfonyl group, or the like.

In the representation of R¹⁶, the C1-C6 alkyl group includes a methylgroup, an ethyl group, a propyl group, an isopropyl group, a butylgroup, an isobutyl group, a sec-butyl group, a tert-butyl group, apentyl group, an isopentyl group, a hexyl group and the like;

-   the C1-C6 haloalkyl group includes a fluoromethyl group, a    difluoromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl    group, a 2,2,2-trifluoroethyl group, a 6,6,6-trifluorohexyl group    and the like;-   the C3-C6 alkenyl group includes a 2-propenyl group, a    1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 2-butenyl    group, a 3-butenyl group, a 2-hexenyl group, a 5-hexenyl group and    the like;-   the C3-C6 haloalkenyl group includes a 2,3-dichloropropenyl group, a    3,3-dichloropropenyl group, a 3,3-difluoropropenyl group and the    like;-   the C3-C6 alkynyl group includes a 2-propynyl group, a    1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a    2-butynyl group, a 3-butynyl group, a 2-hexynyl group, a 5-hexynyl    group and the like;-   the C3-C6 haloalkynyl group includes a 3-chloro-2-propynyl group, a    3-bromo-2-propynyl group, a 6-chloro-5-hexynyl group and the like;    and-   the C3-C6 cycloalkyl group includes a cyclopropyl group, a    cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the    like.

In the representation of R¹⁷, the halogen atom includes a fluorine atom,a chlorine atom, a bromine atom and the like; the C1-C6 alkyl groupincludes a methyl group, an ethyl group, a propyl group, an isopropylgroup, a butyl group, an isobutyl group, a sec-butyl group, a tert-butylgroup, a pentyl group, an isopentyl group, a hexyl group and the like;

-   the C1-C6 haloalkyl group includes a fluoromethyl group, a    difluoromethyl group, a trifluoromethyl group, a chlorofluoromethyl    group, a bromodifluoromethyl group, a 2-fluoroethyl group, a    2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a    6,6,6-trifluorohexyl group and the like;-   the C1-C6 alkoxy group includes a methoxy group, an ethoxy group, a    propoxy group, an isopropoxy group, a butoxy group, an isobutoxy    group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group,    an isopentyloxy group, a hexyloxy group and the like;-   the C1-C6 haloalkoxy group includes a trifluoromethoxy group, a    difluoromethoxy group, a bromodifluoromethoxy group, a    chlorodifluoromethoxy group, a fluoromethoxy group, a    2,2,2-trifluoroethoxy group, a 1,1,2,2-tetrafluoroethoxy group, a    5-chloropentyloxy group, a 4-fluoroisopentyloxy group, a    2,2-dichlorohexyloxy group and the like;-   the C3-C6 alkenyloxy group includes a 2-propenyloxy group, a    1-methyl-2-propenyloxy group, a 2-methyl-2-propenyloxy group, a    2-butenyloxy group, a 3-butenyloxy group, a 2-hexenyloxy group, a    5-hexenyloxy group and the like;-   the C3-C6 haloalkenyloxy group includes a 3,3-dichloro-2-propynyloxy    group, a 3-chloro-2-propynyloxy group, a 3-bromo-2-propynyloxy    group, a 3-iodo-2-propynyloxy group, a 6-chloro-5-hexenyloxy group    and the like;-   the C3-C6 alkynyloxy group includes a 2-propynyloxy group, a    1-methyl-2-propynyloxy group, a 2-butynyloxy group, a 3-butynyloxy    group, a 2-hexynyloxy group, a 5-hexynyloxy group and the like; and-   the C3-C6 haloalkynyloxy group includes a 3-chloro-2-propynyloxy    group, a 3-bromo-2-propynyloxy group, a 3-iodo-2-propynyloxy group,    a 6-chloro-5-hexynyloxy group and the like;-   the C3-C6 cycloalkyloxy group includes a cyclopropyloxy group, a    cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group    and the like.

In the representation of R¹⁸, the halogen atom includes a fluorine atom,a chlorine atom, a bromine atom and the like;

-   the C1-C6 alkyl group includes a methyl group, an ethyl group, a    propyl group, an isopropyl group, a butyl group, a isobutyl group, a    sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl    group, a hexyl group and the like; and-   the C1-C6 haloalkyl group includes a trifluoromethyl group, a    chlorofluoromethyl group, a bromodifluoromethyl group, a    2-fluoroethyl group, a 2,2-difluoroethyl group, a    2,2,2-trifluoroethyl group, a 6,6,6-trifluorohexyl group and the    like.

In the representation of R¹⁹ and R²⁰, the C1-C6 alkyl group includes amethyl group, an ethyl group, a propyl group, an isopropyl group, abutyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, apentyl group, an isopentyl group, a hexyl group and the like;

-   the C1-C6 haloalkyl group includes a 2-fluoroethyl group, a    2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a    6,6,6-trifluorohexyl group and the like;-   the C3-C6 alkenyl group includes a 2-propenyl group, a    1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 2-butenyl    group, a 3-butenyl group, a 2-hexenyl group, a 5-hexenyl group and    the like;-   the C3-C6 haloalkenyl group includes a 3,3-dichloro-2-propynyl    group, a 3-chloro-2-propynyl group, a 3-bromo-2-propynyl group, a    3-iodo-2-propynyl group, a 6-chloro-5-hexenyl group and the like;-   the C3-C6 alkynyl group includes a 2-propynyl group, a    1-methyl-2-propynyl group, a 2-butynyl group, a 3-butynyl group, a    2-hexynyl group, a 5-hexynyl group and the like; and-   the C3-C6 cycloalkyl group includes a cyclopropyl group, a    cyclopentyl group, a cyclohexyl group and the like.

The embodiment of the compound of the present invention includes, forexample, the following compounds:

-   a phenylpyridine compound represented by the formula (1-1);-   a phenylpyridine compound represented by the formula (1-2);-   a phenylpyridine compound represented by the formula (1-3);-   a phenylpyridine compound represented by the formula (1-4);-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein X is an oxygen atom;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein R⁶ is a hydrogen atom;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein R¹, R², R⁴ and R⁵ are a hydrogen atom;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein R⁹ and R¹⁰ are a C1-C4 alkoxy group; a phenylpyridine    compound represented by any of the formula (1-1) to (1-4) wherein R⁹    and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein X is an oxygen atom and R⁶ is a hydrogen atom;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein X is an oxygen atom, and R¹, R², R⁴ and R⁵ are    hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein X is an oxygen atom, and R⁹ and R¹⁰ are C1-C4 alkoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein X is an oxygen atom, and R⁹ and R¹⁰ are methoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein X is an oxygen atom, R⁶ is a hydrogen atom, and R¹,    R², R⁴ and R⁵ are hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein X is an oxygen atom, R⁶ is a hydrogen atom, and R⁹ and    R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein X is an oxygen atom, R⁶ is a hydrogen atom, and R⁹ and    R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein R⁶ is a hydrogen atom, and R¹, R², R⁴ and R⁵ are    hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein R⁶ is a hydrogen atom, and R⁹ and R¹⁰ are C1-C4 alkoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein R⁶ is a hydrogen atom, and R⁹ and R¹⁰ are methoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein R¹, R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰    are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein R¹, R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰    are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein R¹, R⁴ and R⁵ are hydrogen atoms, R⁶ is a hydrogen    atom, R⁷, R⁸ and R¹¹ are hydrogen atoms, and each of R⁹ and R¹⁰ is a    C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C6 alkenyloxy    group, a C3-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group, a    C3-C6 haloalkynyloxy group, a C2-C6 cyanoalkyloxy group or a C3-C6    cycloalkoxy group;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein R¹, R⁴ and R⁵ are hydrogen atoms, R² is a hydrogen    atom, a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a    C3-C6 alkynyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group,    a C3-C6 alkynyloxy group, a C1-C6 alkylthio group, a C3-C6    cycloalkyl group, a C3-C6 cycloalkoxy group or a cyano group, R⁶ is    a hydrogen atom, R⁷, R⁸ and R¹¹ are hydrogen atoms, and each of R⁹    and R¹⁰ is a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C6    alkenyloxy group, a C3-C6 haloalkenyloxy group, a C3-C6 alkynyloxy    group, a C3-C6 haloalkynyloxy group, a C2-C6 cyanoalkyloxy group or    a C3-C6 cycloalkoxy group;-   a phenylpyridine compound represented by any of the formula (1-1) to    (1-4) wherein R¹, R⁴ and R⁵ are hydrogen atoms, R² is a hydrogen    atom, a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a    C3-C6 alkynyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group,    a C3-C6 alkynyloxy group, a C1-C6 alkylthio group, a C3-C6    cycloalkyl group, a C3-C6 cycloalkoxy group or a cyano group, R⁶ is    a hydrogen atom, R⁷, R⁸ and R¹¹ are hydrogen atoms, and R⁹ and R¹⁰    are C1-C6 alkoxy groups;-   a phenylpyridine compound represented by the formula (1-5);-   a phenylpyridine compound represented by the formula (1-6);-   a phenylpyridine compound represented by the formula (1-7);-   a phenylpyridine compound represented by the formula (1-8);-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom and Z¹ is an oxygen atom;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom and R¹⁵    is a 2-propynyl group;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹, R², R⁴ and R⁵ are hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁹ and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom and R⁶ is a hydrogen atom;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R¹⁴ is a hydrogen atom and Z¹ is    an oxygen atom;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R¹⁴ is a hydrogen atom, Z¹ is an    oxygen atom and R¹⁵ is a 2-propynyl group;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom and R¹, R², R⁴ and R⁵ are hydrogen    atoms;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom and R⁹ and R¹⁰ are C1-C4 alkoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, and R⁹ and R¹⁰ are methoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, R¹⁴ is a    hydrogen atom, and Z¹ is an oxygen atom;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁵ is a hydrogen atom, R¹⁴ is a    hydrogen atom, Z¹ is an oxygen atom, and R¹⁵ is a 2-propynyl group;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁵ is a hydrogen atom, and R¹,    R², R⁴ and R⁵ are hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, and R⁹ and    R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, and R⁹ and    R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, R¹⁴ is a    hydrogen atom, Z¹ is an oxygen atom, and R¹, R², R⁴ and R⁵ are    hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, R¹⁴ is a    hydrogen atom, Z¹ is an oxygen atom, R¹⁵ is a 2-propynyl group, and    R¹, R², R⁴ and R⁵ are hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, R¹⁴ is a    hydrogen atom, Z¹ is an oxygen atom, and R⁹ and R¹⁰ are C1-C4 alkoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, R¹⁴ is a    hydrogen atom, Z¹ is an oxygen atom, R¹⁵ is a 2-propynyl group, and    R⁹ and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, R¹⁴ is a    hydrogen atom, Z¹ is an oxygen atom, and R⁹ and R¹⁰ are methoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, R¹⁴ is a    hydrogen atom, Z¹ is an oxygen atom, R¹⁵ is a 2-propynyl group, and    R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, R¹⁴ is a    hydrogen atom, Z is an oxygen atom, R¹, R², R⁴ and R⁵ are hydrogen    atoms, and R⁹ and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, R¹⁴ is a    hydrogen atom, Z¹ is an oxygen atom, R¹⁵ is a 2-propynyl group, R¹;    R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰ are C1-C4 alkoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, R¹⁴ is a    hydrogen atom, Z¹ is an oxygen atom, R¹, R², R⁴ and R⁵ are hydrogen    atoms, and R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein X is an oxygen atom, R⁶ is a hydrogen atom, R¹⁴ is a    hydrogen atom, Z¹ is an oxygen atom, R¹⁵ is a 2-propynyl group, R¹,    R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, R¹⁴ is a hydrogen atom, and Z¹    is an oxygen atom;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, R¹⁴ is a hydrogen atom, Z¹ is    an oxygen atom, and R¹⁵ is a 2-propynyl group;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, and R¹, R², R⁴ and R⁵ are    hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, and R⁹ and R¹⁰ are C1-C4 alkoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, and R⁹ and R¹⁰ are methoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, R¹⁴ is a hydrogen atom, Z¹ is    an oxygen atom, and R¹, R², R⁴ and R⁵ are hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹ is a hydrogen atom, R¹⁴ is a hydrogen atom, Z¹ is    an oxygen atom, R¹⁵ is a 2-propynyl group, and R¹, R², R⁴ and R⁵ are    hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, R¹⁴ is a hydrogen atom, Z¹ is    an oxygen atom, and R⁹ and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, R¹⁴ is a hydrogen atom, Z¹ is    an oxygen atom, R¹⁵ is a 2-propynyl group, and R⁹ and R¹⁰ are C1-C4    alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, R¹⁴ is a hydrogen atom, Z¹ is    an oxygen atom, and R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, R¹⁴ is a hydrogen atom, Z¹ is    an oxygen atom, R¹⁵ is a 2-propynyl group, and R⁹ and R¹⁰ are    methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, R¹⁴ is a hydrogen atom, Z¹ is    an oxygen atom, R¹, R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰    are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, R¹⁴ is a hydrogen atom, Z¹ is    an oxygen atom, R¹⁵ is a 2-propynyl group, R¹, R², R⁴ and R⁵ are    hydrogen atoms, and R⁹ and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, R¹⁴ is a hydrogen atom, Z¹ is    an oxygen atom, R¹, R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰    are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R⁶ is a hydrogen atom, R¹⁴ is a hydrogen atom, Z¹ is    an oxygen atom, R¹⁵ is a 2-propynyl group, R¹, R², R⁴ and R⁵ are    hydrogen atoms, and R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom, and R¹,    R², R⁴ and R⁵ are hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom, R¹⁵ is a    2-propynyl group, and R¹, R², R⁴ and R⁵ are hydrogen atoms; a    phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom, and R⁹    and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom, R¹⁵ is a    2-propynyl group, and R⁹ and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom, and R⁹    and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom, R¹⁵ is a    2-propynyl group, and R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom, R¹, R²,    R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰ are C1-C4 alkoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom, R¹⁵ is a    2-propynyl group, R¹, R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and    R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom, R¹, R²,    R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom, R¹⁵ is a    2-propynyl group, R¹, R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and    R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹, R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰    are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹, R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰    are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹, R⁴ and R⁵ are a hydrogen atom, R⁶ is a hydrogen    atom, R⁷, R⁸ and R¹¹ are hydrogen atoms, and each of R⁹ and R¹⁰ is a    C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C6 alkenyloxy    group, a C3-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group, a    C3-C6 haloalkynyloxy group, a C2-C6 cyanoalkyloxy group or a C3-C6    cycloalkoxy group, R¹⁴ is a hydrogen atom, Z¹ is an oxygen atom, R¹⁵    is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a    C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynyl    group, a C3-C6 haloalkynyl group or a C3-C6 cycloalkyl group;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹, R⁴ and R⁵ are hydrogen atoms, R² is a hydrogen    atom, a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a    C3-C6 alkynyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group,    a C3-C6 alkynyloxy group, a C1-C6 alkylthio group, a C3-C6    cycloalkyl group, a C3-C6 cycloalkoxy group or a cyano group, R⁵ is    a hydrogen atom, R⁷, R⁸ and R¹¹ are hydrogen atoms, and each of R⁹    and R¹⁰ is a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C6    alkenyloxy group, a C3-C6 haloalkenyloxy group, a C3-C6 alkynyloxy    group, a C3-C6 haloalkynyloxy group, a C2-C6 cyanoalkyloxy group or    a C3-C6 cycloalkoxy group, R¹⁴ is a hydrogen atom, Z¹ is an oxygen    atom, R¹⁵ is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl    group, a C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a C3-C6    alkynyl group, a C3-C6 haloalkynyl group or a C3-C6 cycloalkyl    group;-   a phenylpyridine compound represented by any of the formula (1-5) to    (1-8) wherein R¹, R⁴ and R⁵ are hydrogen atoms, R² is a hydrogen    atom, a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a    C3-C6 alkynyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group,    a C3-C6 alkynyloxy group, a C1-C6 alkylthio group, a C3-C6    cycloalkyl group, a C3-C6 cycloalkoxy group or a cyano group, R⁵ is    a hydrogen atom, R⁷, R⁸ and R¹¹ are hydrogen atoms, and R⁹ and R¹⁰    are C1-C6 alkoxy groups, R¹⁴ is a hydrogen atom, Z¹ is an oxygen    atom, R¹⁵ is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6    alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynyl group, a    C3-C6 haloalkynyl group or a C3-C6 cycloalkyl group:-   a phenylpyridine compound represented by the formula (1-9);-   a phenylpyridine compound represented by the formula (1-10);-   a phenylpyridine compound represented by the formula (1-11);-   a phenylpyridine compound represented by the formula (1-12);-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁶ is a hydrogen atom;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein Z² is NOR¹⁶; a phenylpyridine compound represented by    any of the formula (1-9) to (1-12) wherein R¹, R², R⁴ and R⁵ are    hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁹ and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom and R⁶ is a hydrogen atom;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom and Z² is NOR¹⁶;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom, and R¹, R², R⁴ and R⁵ are    hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom, and R⁹ and R¹⁰ are C1-C4 alkoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom, and R⁹ and R¹⁰ are methoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom, R⁶ is a hydrogen atom, and Z² is    NOR¹⁶;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom, R⁶ is a hydrogen atom, and R¹,    R², R⁴ and R⁵ are hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom, R⁶ is a hydrogen atom, and R⁹    and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom, R⁶ is a hydrogen atom, and R⁹    and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom, R⁶ is a hydrogen atom, Z² is    NOR¹⁶, and R¹, R², R⁴ and R⁵ are hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom, R⁶ is a hydrogen atom, Z² is    NOR¹⁶, and R⁹ and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein X is an oxygen atom, R⁶ is a hydrogen atom, Z² is    NOR¹⁶, and R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁶ is a hydrogen atom, and Z² is NOR¹⁶;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁶ is a hydrogen atom, and R¹, R², R⁴ and R⁵ are    hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁶ is a hydrogen atom, and R⁹ and R¹⁰ are C1-C4    alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁶ is a hydrogen atom, and R⁹ and R¹⁰ are methoxy    groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁶ is a hydrogen atom, Z² is NOR¹⁶, and R¹, R², R⁴    and R⁵ are hydrogen atoms;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁶ is a hydrogen atom, Z² is NOR¹⁶, and R⁹ and R¹⁰    are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁵ is a hydrogen atom, Z² is NOR¹⁶, and R⁹ and R¹⁰    are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁶is a hydrogen atom, Z² is NOR¹⁶, R¹, R², R⁴ and R⁵    are hydrogen atoms, and R⁹ and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R⁶ is a hydrogen atom, Z² is NOR¹⁶, R¹, R², R⁴ and R⁵    are hydrogen atoms, and R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein Z² is NOR¹⁶, and R¹, R², R⁴ and R⁵ are hydrogen    atoms;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein Z² is NOR¹⁶, and R⁹ and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein Z² is NOR¹⁶, and R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein Z² is NOR⁶, R¹, R², R⁴ and R⁵ are hydrogen atoms, and    R⁹ and R¹⁰ are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein Z² is NOR¹, R¹, R², R⁴ and R⁵ are hydrogen atoms,-   and R⁹ and R¹⁰ are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R¹, R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰    are C1-C4 alkoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R¹, R², R⁴ and R⁵ are hydrogen atoms, and R⁹ and R¹⁰    are methoxy groups;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R¹, R⁴ and R⁵ are hydrogen atoms, R⁶ is a hydrogen    atom, R⁷, R⁸ and R¹¹ are hydrogen atoms and each of R⁹ and R¹⁰ is a    C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C6 alkenyloxy    group, a C3-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group, a    C3-C6 haloalkynyloxy group, a C2-C6 cyanoalkyloxy group or a C3-C6    cycloalkoxy group, and Z² is NOR¹⁶;-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R¹, R⁴ and R⁵ are hydrogen atoms, R² is a hydrogen    atom, a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a    C3-C6 alkynyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group,    a C3-C6 alkynyloxy group, a C1-C6 alkylthio group, a C3-C6    cycloalkyl group, a C3-C6 cycloalkoxy group or a cyano group, R⁶ is    a hydrogen atom, R⁷, R⁸ and R¹¹ are hydrogen atoms and each of R⁹    and R¹⁰ is a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C6    alkenyloxy group, a C3-C6 haloalkenyloxy group, a C3-C6 alkynyloxy    group, a C3-C6 haloalkynyloxy group, a C2-C6 cyanoalkyloxy group or    a C3-C6 cycloalkoxy group, and Z² is NOR¹⁶; and-   a phenylpyridine compound represented by any of the formula (1-9) to    (1-12) wherein R¹, R⁴ and R⁵ are hydrogen atoms, R² is a hydrogen    atom, a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a    C3-C6 alkynyl group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group,    a C3-C6 alkynyloxy group, a C1-C6 alkylthio group, a C3-C6    cycloalkyl group, a C3-C6 cycloalkoxy group or a cyano group, R⁶ is    a hydrogen atom, R⁷, R⁸ and R¹¹ are hydrogen atoms and R⁹ and R¹⁰    are C1-C6 alkoxy groups, and Z² is NOR¹⁶.

Methods for producing the compounds of the present invention aredescribed hereinafter.

The compound of the present invention can be produced, for example,according to the following (Production Method 1) to (Production Method12). In these production methods, protecting groups may be, ifnecessary, applied to protect functional groups from chemical reactions.

(Production Method 1)

The compound (4) among the compounds of the present invention can beproduced by subjecting the compound (2) to reaction with the compound(3);

(, wherein, in the formula, L¹ represents a chlorine atom or a bromineatom, R¹, R², R³, R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹¹, W¹—W²═W³—W⁴ and Qrepresent same meaning defined in [Invention 1].)

Said reaction is carried out in the presence of a base and usually in asolvent.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; esters suchas butylacetate, ethylacetate and the like; organic nitriles such asacetonitrile and the like; acid amides such as N,N-dimethylformamide andthe like; sulfoxides such as dimethylsulfoxide and the like; and themixture thereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate and the like; alkali metal hydrides suchas sodium hydride and the like; tertiary amines such as triethylamine,diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene,1,5-diazabicyclo[4.3.0]non-5-ene and the like; and nitrogen-containedaromatic compounds such as pyridine, 4-dimethylaminopyridine and thelike.

The molar ratio applied to the compound (3) is usually from 0.5 to 2moles per 1 mole of the compound (2) and that to the base is 10 moles orless.

The reaction time is usually in the range of from 0.1 to 24 hours, andthe reaction temperature is in the range of from 0 to 150° C.

After completion of the reaction, the compound (4) can be isolated bybeing subjected to post treatment procedure exemplified below.

-   (1) A method to extract reaction mixture with an organic solvent,    followed by the organic layer being dried and concentrated-   (2) A method to filtrate reaction mixture, after addition with an    organic solvent, if necessary, followed by the filtrate being    concentrated-   The isolated compound of the present invention represented by the    formula (4) can be purified by a technique such as chromatography,    recrystallization and the like.    (Production Method 2)

The compound (6) among the compounds of the present invention can beproduced by subjecting the compound (5) to reaction with2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (,which is referred to as “Lawesson's reagent” hereinafter);

(, wherein, in the formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰,R¹¹, W¹—W²═W³—W⁴ and Q represent same meaning defined in [Invention 1].)

Said reaction is usually carried out in a solvent.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, t-butylmethylethers andthe like; aliphatic hydrocarbons such as hexane, heptane and the like;aromatic hydrocarbons such as toluene, xylene and the like; halogenatedhydrocarbons such as chlorobenzene and the like; organic nitriles suchas acetonitrile, butyronitrile and the like; sulfoxides such asdimethylsulfoxide and the like; and the mixture thereof.

Lawesson's reagent is usually used in the molar ratio of from 1 to 10moles per 1 mole of the compound (5).

The reaction time is usually in the range of from 0.5 to 24 hours, andthe reaction temperature is in the range of from 30 to 150° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (6). The isolated compound (6) can be purified by a techniquesuch as chromatography, recrystallization and the like.

(Production Method 3)

The compound (9) among the compounds of the present invention can beproduced by subjecting the compound (7) to reaction with the compound(8);

(, wherein, in the formula, L² represents a bromine atom, an iodine atomor a methanesulfonyloxy group, R⁶⁻¹ represents a C1-C3 alkyl group, R¹,R²R³, R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹¹, w¹—W²═W³—W⁴ and Q represent samemeaning defined in [Invention 1], and X represents same meaningdescribed above.)

Said reaction is carried out in the presence of a base and usually in asolvent.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons chlorobenzene and the like; esters such asbutylacetate, ethylacetate and the like; organic nitrites such asacetonitrile and the like; acid amides such as N,N-dimethylformamide andthe like; sulfoxides such as dimethylsulfoxide and the like; and themixture thereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate and the like; alkali metal hydrides suchas sodium hydride and the like; and tertiary amines such astriethylamine, diisopropylethylamine,1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene andthe like.

The molar ratio applied to the compound (8) is usually from 1 to 10moles per 1 mole of the compound (7) and that to the base is usuallyfrom 1 to 10 moles.

The reaction time is usually in the range of from 0.5 to 24 hours, andthe reaction temperature is in the range of from 0 to 120° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (9). The isolated compound (9) can be purified by a techniquesuch as chromatography, recrystallization and the like.

(Production Method 4)

The compound (11) among the compounds of the present invention can beproduced by subjecting the compound (10) to reaction with a reducingagent;

(, wherein, in the formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹and W¹—W²═W³—W⁴ represent same meaning defined in [Invention 1], and Xrepresents same meaning described above.)

Said reaction is usually carried out in a solvent.

The reducing agent used for the reaction includes sodium borohydride orpotassium borohydride.

The solvent used for the reaction includes alcohols such as methanol,ethanol, 2-propanol and the like; ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like; andwater and the mixture thereof.

The molar ratio applied to the reducing agent is usually from 0.25 to 3moles per 1 mole of the compound (10).

The reaction time is usually in the range of from the instant to 24hours, and the reaction temperature is in the range of from −20 to 100°C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as, after being added with an acidic watersuch as aqueous saturated ammonium chloride, extracting with organicsolvent, subsequently drying and concentrating the organic layerobtained, to isolate the compound (11). The isolated compound (11) canbe purified by a technique such as chromatography, recrystallization andthe like.

(Production Method 5)

The compound (12) among the compounds of the present invention can beproduced by subjecting the compound (10) to reaction with organic metalcompounds such as alkylmagnesium halide (Grignard reagent), alkyllithiumand the like which correspond to R¹⁴⁻¹;

(, wherein, in the formula, R¹⁴⁻¹ represents a C1-C3 alkyl group, R¹,R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹ and W¹—W²═W³—W⁴ represent samemeaning defined in [Invention 1], and X represents same meaningdescribed above.)

Said reaction is usually carried out in a solvent.

The organic metal compound corresponding to R¹⁴⁻¹ used in the reactionis defined by an organic metal compound in which R¹⁴⁻¹ is the organicgroup coupled with a metal element, and is illustrated by alkylmagnesiumhalide and alkyllithium. Specifically included aremethylmagnesiumbromide, methyllithium, ethylmagnesiumchloride andethyllithium.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; and aromatic hydrocarbons such as toluene, xylene and the like.

The molar range applied to the organic metal compound is usually from 1to 3 moles per 1 mole of the compound (10).

The reaction time is usually in the range of from the instant to 24hours, and the reaction temperature is in the range of from −80 to 50°C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (12). The isolated compound (12) can be purified by a techniquesuch as chromatography, recrystallization and the like.

(Production Method 6)

The compound (14) and the compound (16) among the compounds of thepresent invention can be produced by the following method. That is, thecompound (14) can be produced by subjecting the compound (13) toreaction with an alkylsulfonyl chloride compound (Step 6-1), andfurthermore, the compound (16) can be produced by subjecting thecompound (14) to reaction with the compound (15) (Step 6-2);

(, wherein, in the formula, R³³ represents a C1-C3 alkyl group, R¹, R²,R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹⁴, R¹⁵ and W¹—W²═W³—W⁴ representsame meaning defined in [Invention 1], and X and Z¹ represent samemeaning described above.)(Step 6-1)

Said reaction is carried out in the presence of a base and usually in asolvent.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; esters suchas butylacetate, ethylacetate and the like; organic nitrites such asacetonitrile and the like; acid amides such as N,N-dimethylformamide andthe like; sulfoxides such as dimethylsulfoxide and the like; and themixture thereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate and the like; alkali metal hydrides suchas sodium hydride and the like; tertiary amines such as triethylamine,diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene,1,5-diazabicyclo[4.3.0]non-5-ene and the like; and nitrogen-containedaromatic compounds such as pyridine, 4-dimethylaminopyridine and thelike.

The molar ratio applied to the alkylsulfonyl chloride compound isusually from 1 to 3 moles per 1 mole of the compound (13) and that tothe base is usually from 1 to 10 moles.

The reaction time is usually in the range of from 0.1 to 24 hours, andthe reaction temperature is in the range of from −20 to 100° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent, ifnecessary, after the organic layer being washed by acidic water, basicwater or the like, subsequently drying and concentrating the organiclayer, to isolate the compound (14). The isolated compound (14) can bepurified by a technique such as recrystallization and the like.

(Step 6-2)

Said reaction is carried out with or without the presence of a solventwith or without the presence of a base.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; esters suchas butylacetate, ethylacetate and the like; organic nitrites such asacetonitrile and the like; acid amides such as N,N-dimethylformamide andthe like; sulfoxides such as dimethylsulfoxide and the like; and themixture thereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate and the like; alkali metal hydrides suchas sodium hydride and the like; tertiary amines such as triethylamine,diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene,1,5-diazabicyclo[4.3.0]non-5-ene and the like; and nitrogen-containedaromatic compounds such as pyridine, 4-dimethylaminopyridine and thelike.

The molar ratio applied to the compound (15) is usually from 1 mole toexcessive amount per 1 mole of the compound (14). The reaction time isusually in the range of from 0.5 to 24 hours, and the reactiontemperature is in the range of from 0 to 150° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent, ifnecessary, after the organic layer being washed by acidic water, basicwater or the like, subsequently drying and concentrating the organiclayer, to isolate the compound (16). The isolated compound (16) can bepurified by a technique such as recrystallization and the like.

(Production Method 7)

The compound (19) among the compounds of the present invention can beproduced by subjecting the compound (17) to reaction with the compound(18) or the salt thereof;

(, wherein, in the formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰,R¹¹, R¹⁶ and W¹—W²═W³—W⁴ represent same meaning defined in [Invention1], and X represents same meaning described above.)

Said reaction is usually carried out in a solvent, and if necessary, inthe presence of a base.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; esters suchas butylacetate, ethylacetate and the like; alcohols such as methanol,ethanol, propanol and the like; organic nitrites such as acetonitrileand the like; acid amides such as N,N-dimethylformamide and the like;sulfoxides such as dimethylsulfoxide and the like; and the mixturethereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate, sodium bicarbonate and the like;tertiary amines such as triethylamine, diisopropylethylamine,1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene andthe like; and nitrogen-contained aromatic compounds such as pyridine,4-dimethylaminopyridine and the like.

The molar range applied to the base is usually from the catalytic amountto 10 moles per 1 mole of the compound (17) and that to the compound(18) or the salt thereof is usually from 1 to 10 moles.

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from 0 to 150° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent, and ifnecessary, after the organic layer being washed by acidic water, andsubsequently drying and concentrating the organic layer, to isolate thecompound (19). The isolated compound (19) can be purified by a techniquesuch as chromatography, recrystallization and the like.

(Production Method 8)

The compound (22) among the compounds of the present invention can beproduced by subjecting the compound (20) to reaction with the compound(21):

(, wherein, in the formula, L³ represents a chlorine atom, a bromineatom and a methanesulfonyloxy group; R¹⁵⁻¹ represents a C1-C6 alkylgroup, a C1-C6 haloalkyl group, a C3-C6 alkenyl group, a C3-C6haloalkenyl group, a C3-C6 alkynyl group, a C3-C6 haloalkynyl group, aC3-C6 cycloalkyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6haloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6haloalkoxy)carbonyl group, a (C3-C6 alkenyloxy)carbonyl group, a (C3-C6haloalkenyloxy)carbonyl group, a (C3-C6 alkynyloxy)carbonyl group, a(C3-C6 haloalkynyloxy) carbonyl group or a C1-C3 alkylsulfonyl group;R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹⁴, W¹—W²═W³—W⁴ and Xrepresent same meaning defined in [Invention 1]; and Z¹ represents samemeaning described above.)

Said reaction is usually carried out in a solvent with the presence of abase.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; esters suchas butylacetate, ethylacetate and the like; organic nitriles such asacetonitrile and the like; acid amides such as N,N-dimethylformamide andthe like; sulfoxides such as dimethylsulfoxide and the like; and waterand the mixture thereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate and the like; alkali metal hydrides suchas sodium hydride and the like; tertiary amines such as triethylamine,diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene,1,5-diazabicyclo[4.3.0]non-5-ene and the like; and nitrogen-containedaromatic compounds such as pyridine, 4-dimethylaminopyridine and thelike.

The molar range applied to the compound (21) is usually from 1 to 3moles per 1 mole of the compound (20) and that to the base is usuallyfrom 1 to 3 moles.

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from 0 to 150° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (22). The isolated compound (22) can be purified by a techniquesuch as chromatography, recrystallization and the like.

(Production Method 9)

The compound (28) among the compounds of the present invention can beproduced by subjecting the compound (26) to reaction with the compound(27);

(, wherein, in the formula, L⁵ represents a chlorine atom, a bromineatom or an iodine atom, and R¹, R², R³, R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹¹ andW¹—W²═W³—W⁴ represent same meaning defined in [Invention 1].)

Said reaction is carried out in a solvent with the presence of acatalyst.

The solvent used for the reaction includes alcohols such as methanol,ethanol, propanol, butanol, 2-propanoland and the like; ethers such as1,4-dioxane, tetrahydrofuran, ethyleneglycoldimethylether,tert-butylmethylether and the like; aliphatic hydrocarbons such ashexane, heptane, octane and the like; aromatic hydrocarbons such astoluene, xylene and the like; water and the mixture thereof.

The catalyst used for the reaction includes palladium acetate,tetrakistriphenylphosphine palladium,{1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium methylenechloride complex and bis (triphenylphosphine) palladium dichloride.

The molar range applied to the compound (27) is usually from 1 to 5moles per 1 mole of the compound (26) and that to the catalyst isusually from 0.001 to 0.1 moles.

Said reaction may be, if necessary, carried out in the presence of abase (, which includes inorganic base such as sodium acetate, potassiumacetate, potassium carbonate, tripotassium phosphate, sodium bicarbonateand the like) and/or a phase-transfer catalyst (, which includesquaternary ammonium salts such as tetrabutylammonium bromide,benzyltriethylammonium bromide and the like).

The reaction time is usually in the range of from 0.5 to 24 hours, andthe reaction temperature is in the range of from 50 to 120° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as filtrating as itself, subsequentlyconcentrating the filtrate, to isolate the compound (28). The isolatedcompound (28) can be purified by a technique such as chromatography,recrystallization and the like.

(Production Method 10)

The compound (42) among the compounds of the present invention can beproduced by subjecting the compound (40) to reaction with the compound(41):

(, wherein, in the formula, L⁹ represents a chlorine atom, a bromineatom and a methanesulfonyloxy group; R¹⁶⁻¹ represents a C1-C6 alkylgroup, a C1-C6 haloalkyl group, a C3-C6 alkenyl group, a C3-C6haloalkenyl group, a C3-C6 alkynyl group, a C3-C6 haloalkynyl group or aC3-C6 cycloalkyl group; R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹ andW¹—W²═W³—W⁴ represent same meaning defined in [Invention 1]; and Xrepresents same meaning described above.)

Said reaction is usually carried out in a solvent with the presence of abase.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons chlorobenzene and the like; esters such asbutylacetate, ethylacetate and the like; organic nitriles such asacetonitrile and the like; acid amides such as N,N-dimethylformamide andthe like; sulfoxides such as dimethylsulfoxide and the like; and themixture thereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate and the like; and alkali metal hydridessuch as sodium hydride and the like.

The molar range applied to the compound (41) is usually from 1 to 3moles per 1 mole of the compound (40) and that to the base is usuallyfrom 1 to 10 moles.

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from 0 to 150° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (42). The isolated compound (42) can be purified by a techniquesuch as chromatography, recrystallization and the like.

(Production Method 11)

The compound (45) among the compounds of the present invention can beproduced by subjecting the compound (43) to reaction with the compound(44):

[, wherein, in the formula, L¹⁰ represents leaving groups such as achlorine atom, a bromine atom, an iodine atom, p-toluenesulfonyloxygroup, a methanesulfonyloxy group and the like; R³⁴ represents a C1-C6alkyl group, a C1-C6 haloalkyl group, a C3-C6 alkenyl group, a C3-C6haloalkenyl group, a C3-C6 alkynyl group, a C3-C6 haloalkynyl group or aC3-C6 cycloalkyl group; R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹ andW¹—W²═W³—W⁴ represent same meaning defined in [Invention 1]; and Xrepresents same meaning described above.)

Said reaction is usually carried out in a solvent with the presence of abase.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; esters suchas butylacetate, ethylacetate and the like; organic nitrites such asacetonitrile and the like; acid amides such as N,N-dimethylformamide andthe like; sulfoxides such as dimethylsulfoxide and the like; and themixture thereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate and the like; alkali metal hydrides suchas sodium hydride and the like; tertiary amines such as triethylamine,diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene,1,5-diazabicyclo[4.3.0]non-5-ene and the like; and nitrogen-containedaromatic compounds such as pyridine, 4-dimethylaminopyridine and thelike.

The molar range applied to the compound (44) is usually from 1 to 3moles per 1 mole of the compound (43) and that to the base is usuallyfrom 1 to 5 moles.

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from 0 to 150° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (45). The isolated compound (45) can be purified by a techniquesuch as chromatography, recrystallization and the like.

(Production Method 12)

The compound (52) among the compounds of the present invention can beproduced by subjecting the compound (25) to reaction with the compound(18) or the salt thereof to obtain the compound (51) (Step 12-1), andthen subjecting the compound (51) to reaction with the compound (27)(Step 12-2);

(wherein, in the formula, R¹, R², R³, R⁴, R⁵, R⁷, R⁸, R⁹, R¹⁰, R¹¹ andW¹—W²═W³—W⁴ represent same meaning defined in [Invention 1], and R¹⁶ andL⁵ represent same meaning described above.)(Step 12-1)

Said reaction is usually carried out in a solvent, and if necessary, inthe presence of a base.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; estersbutylacetate, ethylacetate and the like; alcohols such as methanol,ethanol, propanol and the like; organic nitrites such as acetonitrileand the like; acid amides such as N,N-dimethylformamide and the like;sulfoxides such as dimethylsulfoxide and the like; and the mixturethereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate, sodium bicarbonate and the like;tertiary amines such as triethylamine, diisopropylethylamine,1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene andthe like; and nitrogen-contained aromatic compounds such as pyridine,4-dimethylaminopyridine and the like.

The molar range applied to the base is usually from the catalytic amountto 10 moles per 1 mole of the compound (25) and that to the compound(18) or the salt thereof is usually from 1 to 10 moles.

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from 0 to 150° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent, and ifnecessary, the organic layer being washed by acidic water and the like,subsequently drying and concentrating the organic layer, to isolate thecompound (51). The isolated compound (51) can be purified by a techniquesuch as chromatography, recrystallization and the like.

(Step 12-2)

Said reaction is carried out in a solvent with the presence of acatalyst.

The solvent used for the reaction includes alcohols such as methanol,ethanol, propanol, butanol, 2-propanol and the like; ethers such as1,4-dioxane, tetrahydrofuran, ethyleneglycoldimethylether,tert-butylmethylether and the like; aliphatic hydrocarbons such ashexane, heptane, octane and the like; aromatic hydrocarbons such astoluene, xylene and the like; water and the mixture thereof.

The catalyst used for the reaction includes palladium acetate,tetrakistriphenylphosphine palladium,{1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium methylenechloride complex and bis (triphenylphosphine) palladium dichloride.

The molar range applied to the compound (27) is usually from 1 to 5moles per 1 mole of the compound (51) and that to the catalyst isusually from 0.001 to 0.1 moles.

Said reaction may be, if necessary, carried out in the presence of abase (, which includes inorganic base such as sodium acetate, potassiumacetate, potassium carbonate, tripotassium phosphate, sodium bicarbonateand the like) and/or a phase-transfer catalyst (, which includesquaternary ammonium salts such as tetrabutylammonium bromide,benzyltriethylammonium bromide and the like).

The reaction time is usually in the range of from 0.5 to 24 hours, andthe reaction temperature is in the range of from 50 to 120° C.

After completion of the reaction, the compound (52) can be isolated bybeing subjected to post treatment procedure exemplified below.

-   (1) A method to extract reaction mixture with an organic solvent,    followed by the organic layer obtained being dried and concentrated-   (2) A method to filtrate reaction mixture, after addition with an    organic solvent, if necessary, followed by the filtrate being    concentrated

The isolated compound (52) can be purified by technique such aschromatography, recrystallization and the like.

Next, methods for producing intermediate compounds of the compound ofthe present invention are described as follows.

The compound (3) can be produced, for example, according to thefollowing (Intermediate Compound Production Method 1) or (IntermediateCompound Production Method 2).(Intermediate Compound Production Method 1)

(, wherein, in the formula, L⁶ represents a chlorine atom, a bromineatom and an iodine atom; and R⁷, R⁸, R⁹, R¹⁰, R¹¹ and W¹—W²═W³—W⁴represent same meaning defined in [Invention 1].)(Step I-1)

The compound (30) can be produced by subjecting the compound (29) toreaction with the compound (27).

Said reaction is carried out in a solvent with the presence of acatalyst.

The solvent used for the reaction includes, alcohols such as methanol,ethanol, propanol, butanol, 2-propanoland and the like; ethers such as1,4-dioxane, tetrahydrofuran, ethyleneglycoldimethylether,tert-butylmethylether and the like; aliphatic hydrocarbons such ashexane, heptane, octane and the like; aromatic hydrocarbons such astoluene, xylene and the like; water and the mixture thereof.

The catalyst used for the reaction includes palladium acetate,tetrakistriphenylphosphine palladium,{1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium methylenechloride complex and bis(triphenylphosphine) palladium dichloride.

The molar ratio applied to the compound (27) is usually from 1 to 5moles per 1 mole of the compound (29) and that to the catalyst isusually from 0.001 to 0.1 moles.

Said reaction may be, if necessary, carried out in the presence of abase (, which includes inorganic base such as sodium acetate, potassiumacetate, potassium carbonate, tripotassium phosphate, sodium bicarbonateand the like) and/or a phase-transfer catalyst (, which includesquaternary ammonium salts such as tetrabutylammonium bromide,benzyltriethylammonium bromide and the like).

The reaction time is usually in the range of from 0.5 to 24 hours, andthe reaction temperature is in the range of from 50 to 120° C.

After completion of the reaction, the compound (30) can be isolated bybeing subjected to post treatment procedure exemplified below.

-   (1) A method to extract the reaction mixture with an organic    solvent, followed by the organic layer being dried and concentrated-   (2) A method to filtrate the reaction mixture, after addition with    an organic solvent, if necessary, followed by the filtrate being    concentrated

The isolated compound (30) can be purified by a techniquechromatography, recrystallization and the like.

(Step I-2)

The compound (3) can be produced by subjecting the compound (30) toreduction reaction.

Said reduction reaction includes a method to reduce the compound (30) byhydrogen in the presence of hydrogenation catalyst (, said method isreferred to as (Step I-2-1) hereinafter), and a method to reduce thecompound (30) by iron in the presence of an acidic water (, said methodis referred to as (Step I-2-2) hereinafter).

(Step I-2-1)

The reaction of this step is usually carried out in a solvent.

The solvent used for the reaction of the present step includes alcoholssuch as methanol, ethanol and the like; and ethers such as 1,4-dioxane,tetrahydrofuran and the like.

The hydrogenation catalyst used for the reaction includes palladiumcatalysts such as palladium-carbon and platinum catalysts such asplatinum-carbon.

The molar ratio applied to hydrogen is usually from 3 to 10 moles per 1mole of the compound (30) and that to the catalyst is usually from 0.001to 0.1 moles.

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from 20 to 50° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as filtrating, subsequently concentratingthe filtrate, to isolate the compound (3). The isolated compound (3) canbe purified by a technique such as chromatography, recrystallization andthe like.

(Step I-2-2)

The acidic waters used for the reaction in this step include aqueousacetic acid, diluted hydrochloric acid, aqueous sulfuric acid and thelike. The reaction may be, if necessary, carried out in the presence ofesters such as ethylacetate and the like; and ethers such astetrahydrofuran and the like. The iron used for the reaction is usuallyused in the form of powder.

The molar ratio applied to the iron is usually from 6 to 30 moles per 1mole of the compound (30).

The reaction time is usually in the range of from 0.1 to 10 hours, andthe reaction temperature is in the range of from 40 to 100° C.

After completion of the reaction, the reaction mixture is subjected tofiltration, the filtrate obtained being washed by a basic water (such asaqueous saturated sodium bicarbonate and the like) and then beingsubjected to extraction with organic solvent, subsequently drying andconcentrating the organic layer, to isolate the compound (3). Theisolated compound (3) can be purified by a technique such aschromatography, recrystallization and the like.(Intermediate Compound Production Method 2)

(, wherein, in the formula, L⁷ represents a chlorine atom, a bromineatom and an iodine atom, L⁸ represents a C1-C5 alkylcarbonyl group (anacetyl group, a pivaloyl group and the like), and R⁷, R⁸, R⁹, R¹⁰, R¹¹and W¹—W²═W³—W⁴ represent same meaning defined in [Invention 1].)(Step 1]-1)

The compound (32) can be produced by subjecting the compound (31) toreaction with the compound (27).

Said reaction is carried out in a solvent with the presence of acatalyst.

The solvent used for the reaction includes alcohols such as methanol,ethanol, propanol, butanol, 2-propanol and the like; ethers such as1,4-dioxane, tetrahydrofuran, ethyleneglycoldimethylether,tert-butylmethylether and the like; aliphatic hydrocarbons such ashexane, heptane, octane and the like; aromatic hydrocarbons such astoluene, xylene and the like; and water and the mixture thereof.

The catalyst used for the reaction includes palladium acetate,tetrakistriphenylphosphine palladium,{1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium methylenechloride complex and bis(triphenylphosphine) palladium dichloride.

The molar ratio applied to the compound (27) is usually from 1 to 5moles per 1 mole of the compound (31) and that to the catalyst isusually from 0.001 to 0.1 moles.

Said reaction may be, if necessary, carried out in the presence of abase (, which includes inorganic base such as sodium acetate, potassiumacetate, potassium carbonate, tripotassium phosphate, sodium bicarbonateand the like) and/or a phase-transfer catalyst (, which includesquaternary ammonium salts such as tetrabutylammonium bromide,benzyltriethylammonium bromide and the like).

The reaction time is usually in the range of from 0.5 to 24 hours, andthe reaction temperature is in the range of from 50 to 120° C.

After completion of the reaction, the compound (32) can be isolated bybeing subjected to post treatment procedure exemplified below.

-   (1) A method to extract the reaction mixture with an organic    solvent, followed by the organic layer obtained being dried and    concentrated-   (2) A method to filtrate the reaction mixture followed by the    filtrate being concentrated-   (3) A method to concentrate the reaction mixture as itself    The isolated compound (3) can be purified by a technique such as    chromatography, recrystallization and the like.    (Step II-2)

The compound (3) can be produced by subjecting the compound (32) tohydrolysis in the presence of a base (such as sodium hydroxide,potassium hydroxide and the like).

The reaction is carried out in a solvent.

The solvent used for the reaction includes mixtures with water andalcohols such as methanol, ethanol and the like or ethers such as1,4-dioxane and the like.

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from 20 to 100° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (3). The isolated compound (3) can be purified by a techniquesuch as chromatography, recrystallization and the like.

The compound (2) can be produced according to the (Intermediate CompoundProduction Method 3). That is, the compound (2) can be produced bysubjecting the compound (34) to reaction with a halogenating agent (suchas thionyl chloride, thionyl bromide and the like).(Intermediate Compound Production Method 3)

(, wherein, in the formula, L¹ represents a chlorine atom or a bromineatom; and R¹, R², R³, R⁴, R⁵ and Q represent same meaning defined in[Invention 1].)

Said reaction is usually carried out in a solvent.

The solvent used for the reaction includes aromatic hydrocarbons such astoluene, xylene and the like.

The molar ratio applied to the halogenating agent is usually from 1 to 5moles per 1 mole of the compound (34).

The reaction time is usually in the range of from 0.5 to 24 hours, andthe reaction temperature is in the range of from 50 to 120° C.

After completion of the reaction, the compound (2) can be isolated fromthe reaction mixture by being subjected to post treatment procedure suchas concentration and the like.

Some of the compound (34) can be produced according to the methodsdescribed in International Publication WO01/95721, InternationalPublication WO00/41998, International Publication WO96/23763 orInternational Publication WO96/31464.

Furthermore, the compound (50) among the compound (34) can be producedaccording to (Intermediate Compound Production Method 4).(Intermediate Compound Production Method 4)

(, wherein, in the formula, R¹, R², R³, R⁴ and R⁵ represent same meaningdefined in [Invention 1] and R¹⁵ represents same meaning describedabove.)(Step IV-1)

The compound (36) can be produced by subjecting the compound (35) toreact with a reducing agent.

Said reaction is carried out in a solvent.

The reducing agent used for the reaction includes sodium borohydride andpotassium borohydride.

The solvent used for the reaction includes alcohols such as methanol,ethanol, 2-propanol and the like; ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like; andwater and the mixture thereof.

The molar ratio applied to the reducing agent is usually from 0.25 to 3moles per 1 mole of the compound (35).

The reaction time is usually in the range of from the instant to 24hours, and the reaction temperature is in the range of from −20 to 100°C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (36). The isolated compound (36) can be purified by a techniquesuch as chromatography, recrystallization and the like.

(Step IV-2)

The compound (37) can be produced by subjecting the compound (36) toreact with methanesulfonylchloride.

Said reaction is carried out with the presence of a base usually in asolvent.

The solvent used for the reaction includes, ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; estersbutylacetate, ethylacetate and the like; organic nitrites such asacetonitrile and the like; acid amides such as N,N-dimethylformamide andthe like; sulfoxides such as dimethylsulfoxide and the like; and themixture thereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate and the like; alkali metal hydrides suchas sodium hydride and the like; tertiary amines such as triethylamine,diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene,1,5-diazabicyclo[4.3.0]non-5-ene and the like; and nitrogen-containedaromatic compounds such as pyridine, 4-dimethylaminopyridine and thelike.

The molar ratio applied to methanesulfonylchloride is usually from 1 to3 moles per 1 mole of the compound (36) and that of the base is usuallyfrom 1 to 10 moles.

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from −20 to 100° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as concentration, the concentrated residuebeing added with an organic solvent to be filtrated, subsequentlyconcentrating the filtrate, to isolate the compound (37).

(Step IV-3)

The compound (39) can be produced by subjecting the compound (37) toreact with the compound (38).

Said reaction is usually carried out in a solvent with the presence of abase.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; estersbutylacetate, ethylacetate and the like; organic nitrites such asacetonitrile and the like; acid amides such as N,N-dimethylformamide andthe like; sulfoxides such as dimethylsulfoxide and the like; and themixture thereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate and the like; alkali metal hydrides suchas sodium hydride and the like; tertiary amines such as triethylamine,diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene,1,5-diazabicyclo[4.3.0]non-5-ene and the like; and nitrogen-containedaromatic compounds such as pyridine, 4-dimethylaminopyridine and thelike.

The molar ratio applied to the compound (38) is usually from 1 toexcessive amount per 1 mole of the compound (37) and that of the base isusually from the catalytic amount to 5 moles.

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from 50 to 150° C.

After completion of the reaction, the compound (39) can be isolated bybeing subjected to post treatment procedure exemplified below.

-   (1) A method to extract the reaction mixture with an organic    solvent, followed by the organic layer being dried and concentrated-   (2) A method to concentrate the reaction mixture, after addition    with an organic solvent such as toluene or the like if necessary    The isolated compound (39) can be purified by a technique such as    recrystallization and the like.    (Step IV-4)

The compound (50) can be produced by subjecting the compound (39) tohydrolysis in the presence of a base (such as sodium hydroxide,potassium hydroxide and the like).

The reaction is usually carried out in a solvent such as mixture ofwater and an alcohol (, for example, methanol, ethanol and the like) andthe like.

The molar ratio applied to the base is usually from 1 to 20 moles per 1mole of the compound (39).

The reaction time is usually in the range of from 0.5 to 24 hours, andthe reaction temperature is in the range of from 0 to 120° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure, such as, after being made acidity with an acidsuch as hydrochloric acid and the like, extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (50). The isolated compound (50) can be purified by a techniquesuch as chromatography, recrystallization and the like.

The compound (100) in the compound (50) wherein R¹, R⁴ and R⁵ arehydrogen atoms and R¹⁵ is a 2-propynyl group, is one of the importantproduction intermediates in the present invention.

(, wherein, in the formula, R² and R³ independently represent a hydrogenatom, a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, aC2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, aC2-C6 haloalkynyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group,a C3-C6 alkenyloxy group, a C3-C6 haloalkenyloxy group, a C3-C6alkynyloxy group, a C3-C6 haloalkynyloxy group, a C1-C6 alkylthio group,a C1-C6 haloalkylthio group, a C3-C6 cycloalkyl group, a C3-C6cycloalkoxy group or a cyano group; or R² and R³ are combined at theterminals thereof to represent a trimethylene, a tetramethylene or—CH═CH—CH═CH—.)

The compound (43) can be produced according to, for example,(Intermediate Compound Production Method 5).(Intermediate Compound Production Method 5)

[, wherein, in the formula, L¹¹ represents a chlorine atom or a bromineatom; L¹² and L¹³ are same or different each other and represent analkoxy group such as a methoxy group and the like; R¹, R², R³, R⁴, R⁵,R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹ and W¹—W²═W³—W⁴ represent same meaning definedin [Invention 1]; and X represents same meaning described above.](Step V-1)

The compound (48) can be produced by subjecting the compound (46) toreact with the compound (47).

Said reaction is usually carried out in a solvent with the presence of abase.

The solvent used for the reaction includes, ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; estersbutylacetate, ethylacetate and the like; organic nitrites such asacetonitrile and the like; acid amides such as N,N-dimethylformamide andthe like; sulfoxides such as dimethylsulfoxide and the like; and themixture thereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate and the like; alkali metal hydrides suchas sodium hydride and the like; tertiary amines such as triethylamine,diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene,1,5-diazabicyclo[4.3.0]non-5-ene and the like; and nitrogen-containedaromatic compounds such as pyridine, 4-dimethylaminopyridine and thelike.

The molar ratio applied to the compound (47) is usually from 0.5 to 2moles per 1 mole of the compound (46) and that to the base is from 1 to10 moles.

The reaction time is usually in the range of from 0.1 to 24 hours, andthe reaction temperature is in the range of from 0 to 150° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (48). The isolated compound (48) can be purified by a techniquesuch as chromatography, recrystallization and the like.

(Step V-2)

The compound (49) can be produced by subjecting the compound (48) toreact with the compound (48-1) or the compound (48-2).

Said reaction is usually carried out in a solvent.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, t-butylmethylether and thelike, aliphatic hydrocarbons such as hexane, heptane and the like,aromatic hydrocarbons such as toluene and the like, halogenatedhydrocarbons such as chlorobenzene and the like, organic bases such aspyridine, triethylamine, N,N-dimethylaniline and the like,N,N-dimethylformamide or the mixture thereof.

The molar ratio applied to the compound (48-1) or the compound (48-2) isusually from 1 to 10 moles per 1 mole of the compound (48).

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from 50 to 150° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (49). The isolated compound (49) can be purified by a techniquesuch as chromatography, recrystallization and the like.

(Step V-3)

The compound (43) can be produced by subjecting the compound (49) toreact with water in the presence of an acid.

Said reaction may be carried out in water as the solvent or in themixture of water and other organic solvents.

The other organic solvents include ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, t-butylmethylether and thelike, aliphatic hydrocarbons such as hexane, heptane and the like,aromatic hydrocarbons such as toluene and the like, halogenatedhydrocarbons such as chlorobenzene and the like, organic nitrites suchas acetonitrile and the like; N,N-dimethylformamide, dimethylsulfoxideand the mixture thereof.

The acid used for the reaction includes hydrochloric acid, sulfuricacid, p-toluenesulfonic acid and the like.

The molar ratio applied to the acid is usually from 0.1 to 100 moles per1 mole of the compound (49).

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from 20 to 100° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent,subsequently drying and concentrating the organic layer, to isolate thecompound (43). The isolated compound (43) can be purified by a techniquesuch as chromatography, recrystallization and the like.

The compound (26) can be produced according to (Intermediate CompoundProduction Method 6).(Intermediate Compound Production Method 6)

(, wherein, in the formula, L⁴ represents a chlorine atom or a bromineatom, L⁵ represents a chlorine atom, a bromine atom or an iodine atom,and R¹, R², R³, R⁴, R⁵ and W¹—W²═W³—W⁴ represent same meaning defined in[Invention 1].)(Step VI-1)

The compound (25) can be produced by subjecting the compound (23) toreact with the compound (24).

Said reaction is usually carried out in a solvent with the presence of abase.

The solvent used for the reaction includes ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like;halogenated hydrocarbons such as chlorobenzene and the like; esters suchas ethylacetate, butylacetate and the like; organic nitrites such asacetonitrile, butyronitrile and the like; acid amides such asN,N-dimethylformamide and the like; sulfoxides such as dimethylsulfoxideand the like; and the mixture thereof.

The base used for the reaction includes carbonates such as sodiumcarbonate, potassium carbonate and the like; tertiary amines such astriethylamine, diisopropylethylamine,1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene andthe like; and nitrogen-contained aromatic compounds such as pyridine,4-dimethylaminopyridine and the like.

The molar ratio applied to the compound (23) is usually from 1 to 3moles per 1 mole of the compound (23) and that of the base is usuallyfrom 1 to 10 moles.

The reaction time is usually in the range of from 1 to 24 hours, and thereaction temperature is in the range of from −20 to 100° C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent, ifnecessary, the organic layer being washed by acidic water, basic waterand the like, subsequently drying and concentrating the organic layer,to isolate the compound (25). The isolated compound (25) can be purifiedby a technique such as chromatography, recrystallization and the like.

(Step VI-2)

The compound (26) can be produced by subjecting the compound (25) toreact with a reducing agent.

Said reaction is carried out in a solvent.

The reducing agent used for the reaction includes sodium borohydride andpotassium borohydride.

The solvent used for the reaction includes alcohols such as methanol,ethanol, 2-propanol and the like; ethers such as 1,4-dioxane,tetrahydrofuran, ethyleneglycoldimethylether, tert-butylmethylether andthe like; aliphatic hydrocarbons such as hexane, heptane, octane and thelike; aromatic hydrocarbons such as toluene, xylene and the like; waterand the mixture thereof.

The molar ratio applied to the reducing agent is usually from 0.25 to 3moles per 1 mole of the compound (25).

The reaction time is usually in the range of from the instant to 24hours, and the reaction temperature is in the range of from −20 to 100°C.

After completion of the reaction, the reaction mixture is subjected topost treatment procedure such as extracting with organic solvent afterbeing added to an acidic water such as aqueous saturated ammoniumchloride and the like, the organic layer obtained being washed by basicwater, subsequently drying and concentrating the organic layer, toisolate the compound (26). The isolated compound (26) can be purified bya technique such as chromatography, recrystallization and the like.

The specific examples of the compound of the present invention areillustrated below:

-   A compound represented by the formula (I)-   a compound represented by the formula (II)-   a compound represented by the formula (III)-   a compound represented by the formula (IV)

wherein, in the formula (I) to (IV), R^(2a), R^(3a), A¹, A², R^(9a),R^(10a) and X^(a) represent the combination of substituted groupsexhibited in (Table 1). TABLE 1 R^(2a) R^(3a) A¹ A² R^(9a) R^(10a) X^(a)H H H OCH₂C≡CH OCH₃ OCH₃ O H F H OCH₂C≡CH OCH₃ OCH₃ O H Cl H OCH₂C≡CHOCH₃ OCH₃ O H Br H OCH₂C≡CH OCH₃ OCH₃ O H CH₃ H OCH₂C≡CH OCH₃ OCH₃ O HCH₂CH₃ H OCH₂C≡CH OCH₃ OCH₃ O H CH₂CH₂CH₃ H OCH₂C≡CH OCH₃ OCH₃ O HCH(CH₃)₂ H OCH₂C≡CH OCH₃ OCH₃ O H CH═CH₂ H OCH₂C≡CH OCH₃ OCH₃ O H C≡CH HOCH₂C≡CH OCH₃ OCH₃ O H C≡CCH₃ H OCH₂C≡CH OCH₃ OCH₃ O H OCH₃ H OCH₂C≡CHOCH₃ OCH₃ O H OCH₂CH₃ H OCH₂C≡CH OCH₃ OCH₃ O —CH₂CH₂CH₂— H OCH₂C≡CH OCH₃OCH₃ O —CH₂CH₂CH₂CH₂— H OCH₂C≡CH OCH₃ OCH₃ O —CH═CH—CH═CH— H OCH₂C≡CHOCH₃ OCH₃ O CH₃ H H OCH₂C≡CH OCH₃ OCH₃ O Cl H H OCH₂C≡CH OCH₃ OCH₃ O CH₃CH₃ H OCH₂C≡CH OCH₃ OCH₃ O Cl Cl H OCH₂C≡CH OCH₃ OCH₃ O H H H OCH₂C≡CHOCH₃ OCH₃ S H Cl H OCH₂C≡CH OCH₃ OCH₃ S H Br H OCH₂C≡CH OCH₃ OCH₃ S HCH₃ H OCH₂C≡CH OCH₃ OCH₃ S —CH₂CH₂CH₂CH₂— H OCH₂C≡CH OCH₃ OCH₃ S H H HOH OCH₃ OCH₃ O H F H OH OCH₃ OCH₃ O H Cl H OH OCH₃ OCH₃ O H Br H OH OCH₃OCH₃ O H CH₃ H OH OCH₃ OCH₃ O H CH₂CH₃ H OH OCH₃ OCH₃ O H CH₂CH₂CH₃ H OHOCH₃ OCH₃ O H CH(CH₃)₂ H OH OCH₃ OCH₃ O H CH═CH₂ H OH OCH₃ OCH₃ O H C≡CHH OH OCH₃ OCH₃ O H C≡CCH₃ H OH OCH₃ OCH₃ O H OCH₃ H OH OCH₃ OCH₃ O HOCH₂CH₃ H OH OCH₃ OCH₃ O —CH₂CH₂CH₂— H OH OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂— HOH OCH₃ OCH₃ O —CH═CH—CH═CH— H OH OCH₃ OCH₃ O CH₃ H H OH OCH₃ OCH₃ O ClH H OH OCH₃ OCH₃ O CH₃ CH₃ H OH OCH₃ OCH₃ O Cl Cl H OH OCH₃ OCH₃ O H H HOH OCH₃ OCH₃ S H Cl H OH OCH₃ OCH₃ S H Br H OH OCH₃ OCH₃ S H CH₃ H OHOCH₃ OCH₃ S —CH₂CH₂CH₂CH₂— H OH OCH₃ OCH₃ S H H H OCH₃ OCH₃ OCH₃ O H F HOCH₃ OCH₃ OCH₃ O H Cl H OCH₃ OCH₃ OCH₃ O H Br H OCH₃ OCH₃ OCH₃ O H CH₃ HOCH₃ OCH₃ OCH₃ O H CH₂CH₃ H OCH₃ OCH₃ OCH₃ O H CH₂CH₂CH₃ H OCH₃ OCH₃OCH₃ O H CH(CH₃)₂ H OCH₃ OCH₃ OCH₃ O H CH═CH₂ H OCH₃ OCH₃ OCH₃ O H C≡CHH OCH₃ OCH₃ OCH₃ O H C≡CCH₃ H OCH₃ OCH₃ OCH₃ O H OCH₃ H OCH₃ OCH₃ OCH₃ OH OCH₂CH₃ H OCH₃ OCH₃ OCH₃ O —CH₂CH₂CH₂— H OCH₃ OCH₃ OCH₃ O—CH₂CH₂CH₂CH₂— H OCH₃ OCH₃ OCH₃ O —CH═CH—CH═CH— H OCH₃ OCH₃ OCH₃ O CH₃ HH OCH₃ OCH₃ OCH₃ O Cl H H OCH₃ OCH₃ OCH₃ O CH₃ CH₃ H OCH₃ OCH₃ OCH₃ O ClCl H OCH₃ OCH₃ OCH₃ O H H H OCH₃ OCH₃ OCH₃ S H Cl H OCH₃ OCH₃ OCH₃ S HBr H OCH₃ OCH₃ OCH₃ S H CH₃ H OCH₃ OCH₃ OCH₃ S —CH₂CH₂CH₂CH₂— H OCH₃OCH₃ OCH₃ S H H ═NOCH₃ OCH₃ OCH₃ O H F ═NOCH₃ OCH₃ OCH₃ O H Cl ═NOCH₃OCH₃ OCH₃ O H Br ═NOCH₃ OCH₃ OCH₃ O H CH₃ ═NOCH₃ OCH₃ OCH₃ O H CH₂CH₃═NOCH₃ OCH₃ OCH₃ O H CH₂CH₂CH₃ ═NOCH₃ OCH₃ OCH₃ O H CH(CH₃)₂ ═NOCH₃ OCH₃OCH₃ O H CH═CH₂ ═NOCH₃ OCH₃ OCH₃ O H C≡CH ═NOCH₃ OCH₃ OCH₃ O H C≡CCH₃═NOCH₃ OCH₃ OCH₃ O H OCH₃ ═NOCH₃ OCH₃ OCH₃ O H OCH₂CH₃ ═NOCH₃ OCH₃ OCH₃O —CH₂CH₂CH₂— ═NOCH₃ OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂— ═NOCH₃ OCH₃ OCH₃ O—CH═CH—CH═CH— ═NOCH₃ OCH₃ OCH₃ O CH₃ H ═NOCH₃ OCH₃ OCH₃ O Cl H ═NOCH₃OCH₃ OCH₃ O CH₃ CH₃ ═NOCH₃ OCH₃ OCH₃ O Cl Cl ═NOCH₃ OCH₃ OCH₃ O H H═NOCH₃ OCH₃ OCH₃ S H Cl ═NOCH₃ OCH₃ OCH₃ S H Br ═NOCH₃ OCH₃ OCH₃ S H CH₃═NOCH₃ OCH₃ OCH₃ S —CH₂CH₂CH₂CH₂— ═NOCH₃ OCH₃ OCH₃ S H H H OCH₂CH₃ OCH₃OCH₃ O H F H OCH₂CH₃ OCH₃ OCH₃ O H Cl H OCH₂CH₃ OCH₃ OCH₃ O H Br HOCH₂CH₃ OCH₃ OCH₃ O H CH₃ H OCH₂CH₃ OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂— H OCH₂CH₃OCH₃ OCH₃ O H H H OCH₂CF₃ OCH₃ OCH₃ O H F H OCH₂CF₃ OCH₃ OCH₃ O H Cl HOCH₂CF₃ OCH₃ OCH₃ O H Br H OCH₂CF₃ OCH₃ OCH₃ O H CH₃ H OCH₂CF₃ OCH₃ OCH₃O —CH₂CH₂CH₂CH₂— H OCH₂CF₃ OCH₃ OCH₃ O H H H OCH₂CH₂CH₃ OCH₃ OCH₃ O H FH OCH₂CH₂CH₃ OCH₃ OCH₃ O H Cl H OCH₂CH₂CH₃ OCH₃ OCH₃ O H Br H OCH₂CH₂CH₃OCH₃ OCH₃ O H CH₃ H OCH₂CH₂CH₃ OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂— H OCH₂CH₂CH₃OCH₃ OCH₃ O H H H OCH₂CH═CH₂ OCH₃ OCH₃ O H F H OCH₂CH═CH₂ OCH₃ OCH₃ O HCl H OCH₂CH═CH₂ OCH₃ OCH₃ O H Br H OCH₂CH═CH₂ OCH₃ OCH₃ O H CH₃ HOCH₂CH═CH₂ OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂— H OCH₂CH═CH₂ OCH₃ OCH₃ O CH₃ H HOCH₂CH₃ OCH₃ OCH₃ O H H ═NOCH₂CH₃ OCH₃ OCH₃ O H F ═NOCH₂CH₃ OCH₃ OCH₃ OH Cl ═NOCH₂CH₃ OCH₃ OCH₃ O H Br ═NOCH₂CH₃ OCH₃ OCH₃ O H CH₃ ═NOCH₂CH₃OCH₃ OCH₃ O H H ═NOCH₂F OCH₃ OCH₃ O H F ═NOCH₂F OCH₃ OCH₃ O H Cl ═NOCH₂FOCH₃ OCH₃ O H Br ═NOCH₂F OCH₃ OCH₃ O H CH₃ ═NOCH₂F OCH₃ OCH₃ O H H ═CCl₂OCH₃ OCH₃ O H F ═CCl₂ OCH₃ OCH₃ O H Cl ═CCl₂ OCH₃ OCH₃ O H Br ═CCl₂ OCH₃OCH₃ O H CH₃ ═CCl₂ OCH₃ OCH₃ O H H ═CHOCH₂F OCH₃ OCH₃ O H F ═CHOCH₂FOCH₃ OCH₃ O H Cl ═CHOCH₂F OCH₃ OCH₃ O H Br ═CHOCH₂F OCH₃ OCH₃ O H CH₃═CHOCH₂F OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂— ═NOCH₂CH₃ OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂—═NOCH₂F OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂— ═CCl₂ OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂—═CHOCH₂F OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂— ═CCl₂ OCH₃ OCH₃ S H H H OCO₂CH₃ OCH₃OCH₃ O H F H OCO₂CH₃ OCH₃ OCH₃ O H Cl H OCO₂CH₃ OCH₃ OCH₃ O H Br HOCO₂CH₃ OCH₃ OCH₃ O H CH₃ H OCO₂CH₃ OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂— H OCO₂CH₃OCH₃ OCH₃ O H H H OCO₂CH₂CH₃ OCH₃ OCH₃ O H F H OCO₂CH₂CH₃ OCH₃ OCH₃ O HCl H OCO₂CH₂CH₃ OCH₃ OCH₃ O H Br H OCO₂CH₂CH₃ OCH₃ OCH₃ O H CH₃ HOCO₂CH₂CH₃ OCH₃ OCH₃ O —CH₂CH₂CH₂CH₂— H OCO₂CH₂CH₃ OCH₃ OCH₃ O H H HOCH₂C≡CCH₃ OCH₃ OCH₃ O H F H OCH₂C≡CCH₃ OCH₃ OCH₃ O H Cl H OCH₂C≡CCH₃OCH₃ OCH₃ O H Br H OCH₂C≡CCH₃ OCH₃ OCH₃ O H CH₃ H OCH₂C≡CCH₃ OCH₃ OCH₃ O—CH₂CH₂CH₂CH₂— H OCH(CH₃)C≡CCH₃ OCH₃ OCH₃ O H H H OCH(CH₃)C≡CCH₃ OCH₃OCH₃ O H F H OCH(CH₃)C≡CCH₃ OCH₃ OCH₃ O H Cl H OCH(CH₃)C≡CCH₃ OCH₃ OCH₃O H Br H OCH(CH₃)C≡CCH₃ OCH₃ OCH₃ O H CH₃ H OCH(CH₃)C≡CCH₃ OCH₃ OCH₃ O—CH₂CH₂CH₂CH₂— H OCH(CH₃)C≡CCH₃ OCH₃ OCH₃ O —CH₂CH₂CH₂— H OCH₂C≡CCH₃OCH₃ OCH₃ O H H H OCH₂C≡CH OCH₂CH₃ OCH₂CH₃ O H F H OCH₂C≡CH OCH₂CH₃OCH₂CH₃ O H Cl H OCH₂C≡CH OCH₂CH₃ OCH₂CH₃ O H Br H OCH₂C≡CH OCH₂CH₃OCH₂CH₃ O H CH₃ H OCH₂C≡CH OCH₂CH₃ OCH₂CH₃ O —CH₂CH₂CH₂CH₂— H OCH₂C≡CHOCH₂CH₃ OCH₂CH₃ O H H H OCH₂C≡CH OCH₂CH₃ OCH₃ O H F H OCH₂C≡CH OCH₂CH₃OCH₃ O H Cl H OCH₂C≡CH OCH₂CH₃ OCH₃ O H Br H OCH₂C≡CH OCH₂CH₃ OCH₃ O HCH₃ H OCH₂C≡CH OCH₂CH₃ OCH₃ O —CH₂CH₂CH₂CH₂— H OCH₂C≡CH OCH₂CH₃ OCH₃ O HH H OCH₂C≡CH OCH₂C≡CH OCH₃ O H F H OCH₂C≡CH OCH₂C≡CH OCH₃ O H Cl HOCH₂C≡CH OCH₂C≡CH OCH₃ O H Br H OCH₂C≡CH OCH₂C≡CH OCH₃ O H CH₃ HOCH₂C≡CH OCH₂C≡CH OCH₃ O —CH₂CH₂CH₂CH₂— H OCH₂C≡CH OCH₂C≡CH OCH₃ O H H HOCH₂C≡CH OCH₃ OCH₂CH₃ O H F H OCH₂C≡CH OCH₃ OCH₂CH₃ O H Cl H OCH₂C≡CHOCH₃ OCH₂CH₃ O H Br H OCH₂C≡CH OCH₃ OCH₂CH₃ O H CH₃ H OCH₂C≡CH OCH₃OCH₂CH₃ O —CH₂CH₂CH₂CH₂— H OCH₂CH═CH₂ OCH₃ OCH₂CH₃ O H CH₃ H OCH₂C≡CHOCH₂CH₃ OCH₂CH₃ S H H H OCH₂C≡CH OCH₃ OCH₂C≡CH O H F H OCH₂C≡CH OCH₃OCH₂C≡CH O H Cl H OCH₂C≡CH OCH₃ OCH₂C≡CH O H Br H OCH₂C≡CH OCH₃ OCH₂C≡CHO H CH₃ H OCH₂C≡CH OCH₃ OCH₂C≡CH O —CH₂CH₂CH₂CH₂— H OCH₂C≡CH OCH₃OCH₂C≡CH O

Following is the illustration exemplifying the compound (100) which isthe important intermediate in the present invention.

A compound represented by the formula (V)

wherein, in the formula (V), R^(2a), R^(3a), A¹, and A² represent thecombination of substituted groups exhibited in (Table 2). TABLE 2 R^(2a)R^(3a) A¹ A² H H H OCH₂C≡CH H F H OCH₂C≡CH H Cl H OCH₂C≡CH H Br HOCH₂C≡CH H CH₃ H OCH₂C≡CH H CH₂CH₃ H OCH₂C≡CH H CH₂CH₂CH₃ H OCH₂C≡CH HCH(CH₃)₂ H OCH₂C≡CH H CH═CH₂ H OCH₂C≡CH H C≡CH H OCH₂C≡CH H C≡CCH₃ HOCH₂C≡CH H OCH₃ H OCH₂C≡CH H OC₂H₅ H OCH₂C≡CH —CH₂CH₂CH₂— H OCH₂C≡CH—CH₂CH₂CH₂CH₂— H OCH₂C≡CH —CH═CH—CH═CH— H OCH₂C≡CH CH₃ H H OCH₂C≡CH Cl HH OCH₂C≡CH CH₃ CH₃ H OCH₂C≡CH Cl Cl H OCH₂C≡CH

Plant diseases against which the compound of the present invention hascontrolling activity include, for example, a disease due toPhycomycetes, specifically following diseases are illustrated:

Peronospora brassicae of vegetables and radishes; Peronospora spinaciaeof spinach; Peronospora tabacina of tobacco; Pseudoperonospora cubensisof gourds; Plasmopara viticola of grapes; Phytophthora cactorum ofapple, strawberry and ginseng; Phytophora capsici of tomato andcucumber; Phytophthora cinnamomi of pineapple; Phytophthora infestans ofpotato and tomato; Phytophthora nicotianae var. nicotianae of tobacco,broad bean and leek; Pythium sp. of spinach; Pythium aphanidermatum ofcucumber; Pythium sp. of wheat; Pythium debaryanum of tobaco; andPythium rot of soybean (Pythium aphanidermatum, P. debaryanum, P.irregulare, P. myriotylum, P. ultimum).

The fungicidal composition of the present invention comprises thecompound of the present invention and a carrier. The carrier is inert tothe compound of the present invention and appropriately chosen dependingon types applying the fungicidal composition of the present inventionand the like. The fungicidal composition of the present invention mayfurther comprise adjuvant for formulation such as surfactant and thelike depending on the necessity. The fungicidal composition of thepresent invention includes formulation forms such as emulsifiableconcentrate, wettable powder, dry flowable, flowable, dust, granule andthe like. The fungicidal composition of the present invention usuallycontains 0.1 to 90% by weight of the compound of the present invention.

Solid carriers used for the fungicidal composition of the presentinvention include, for example, fine powders or granules of mineralssuch as kaolin clay, attapulgite clay, bentonite, montmorillonite, terraalba, pyrophyllite, talc, diatomaceous earth, calcite and the like;natural organic substancss such as corncob powder, walnut shell powderand the like; synthetic organic substances such as urea and the like;salts such as calcium carbonate, ammonium sulfate and the like;synthetic inorganic substances such as synthetic hydrous silicon oxideand the like. Liquid carriers include, for example, aromatichydrocarbons such as xylene, alkylbenzene, methylnaphthalene and thelike; alcohols such as 2-propanol, ethylene glycol, propylene glycol,cellosolve and the like; ketones such as acetone, cyclohexanone,isophorone and the like; vegetable oils such as soybean oil, cottonseedoil and the like; petroleumaliphatic hydrocarbons, esters,dimethylsulfoxide, acetonitrile and water.

Surfactants include, for example, anionic surfactants such asalkylsulfuric acid ester salt, alkylarylsulfonic acid salt,dialkylsulfosuccinic acid salt, polyoxyethylenealkylaryletherphosphoricacid ester salt, lignin sulfonic acid salt, polycondensednaphthalenesulfonateformaldehyde and the like; and nonionic surfactantssuch as polyoxyethylenealkylarylether,polyoxyethylenealkylpolyoxypropylene block copolymer, sorbitan fattyacid ester and the like.

Another adjuvant for formulation includes, for example, water-solublepolymers such as polyvinylalcohol, polyvinylpyrrolidone and the like;Arabian gum; alginic acid and its salt thereof; polysaccharides such asCMC (carboxymethylcellulose), xanthan gum and the like; inorganicsubstances such as alminum magnesium silicate, alumina sol and the like;and antiseptics, colorants, PAP(isopropyl acidic phosphate), stabilizerssuch as BHT and the like.

By applying the fungicidal composition of the present invention totreatment for plants, said plants can be protected from plant diseases;and by applying the fungicidal composition of the present invention totreatment for soils, said plants grown on said soils can be protectedfrom plant diseases.

When the fungicidal composition of the present invention is applied tofoliage treatment for plants or soil treatment, the application amountthereof, which may be varied with a kind of control-object plants, akind and an infestation level of control-object diseases, formulationtypes, application timings, weather conditions and the like, is usually1 to 5000 g of the compound of the present invention per 10000 m²,preferably 5 to 1000 g.

Emulsifiable concentrate, wettable powder, flowable and the like areusually sprayed after diluted with water. In this case, theconcentration of the compound of the present invention is usually in therange of from 0.0001 to 3% by weight, preferably from 0.0005 to 1% byweight. Dust, granule and the like are usually directly used withoutdilution.

The fungicidal composition of the present invention can be also appliedin treatment methods such as seed disinfection and the like. The methodsinclude, for example, a method to soak seeds of a plant in the liquidfungicidal composition of the present invention which prepared in 1 to1000 ppm in terms of concentration of the compound of the presentinvention, a method to spray or coat seeds of a plant with the liquidfungicidal composition of the present invention which prepared in 1 to1000 ppm in terms of concentration of the compound of the presentinvention, and a method to coat seeds of a plant with the powder of thecomposition controlling plant diseases of the present invention.

The method for controlling plant diseases of the present invention isperformed by applying effective amount of the compound of the presentinvention to a plant or a soil growing the plant in which infection ispredictable and/or to a plant or a soil growing the plant in whichinfection is confirmed.

The fungicidal composition of the present invention is usually used asan agent controlling plant diseases for agriculture or gardening, thatis, as an agent controlling plant diseases to control plant diseases onplowed fields, paddy fields, orchards, tea fields, pastures, lawn andthe like.

The fungicidal composition of the present invention may be used togetherwith other plant disease controlling compositions, pesticides,acaricides, nematicides, herbicides, plant growth regulators and/orfertilizers.

Examples of the active ingredient of such other plant diseasescontrolling composition include:

chlorothalonil; fluazinam; dichlofluanid; fosetyl-Al; cyclic imidederivatives such as captan, captafol, folpet and the like;dithiocarbamate derivatives such asmaneb, mancozeb, thiuram, ziram,zineb, propineb and the like; inorganic or organic copper derivativessuch as basic copper sulfate, basic copper chloride, copper hydroxide,copper-oxinate and the like; acylalanine derivatives such as metalaxyl,furalaxyl, ofurace, cyprofuram, benalaxyl, oxadixyl and the like;strobilurine like compound such as kresoxim-methyl, azoxystrobin,trifloxystrobin, picoxystrobin, pyraclostrobin, dimoxystrobin and thelike; anilinopyrimidine derivatives such as cyprodinil, pyrimethanil,mepanipyrim and the like; phenyl pyrrole derivatives such asfenpiclonil, fludioxonil and the like; imide derivatives such asprocymidone, iprodione, vinclozolin and the like; benzimidazolederivatives such as carbendazim, benomyl, thiabendazole, thiophanatemethyl and the like; amine derivatives such as fenpropimorph,tridemorph, fenpropidin, spiroxamine and the like; azole derivativessuch as propiconazole, triadimenol, prochloraz, penconazole,tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole,difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole,myclobutanil, fenbuconazole, hexaconazole, fluquinconazole,triticonazole, bitertanol, imazalil, flutriafol and the like; cymoxanil;dimethomorph; famoxyadone, fenamidone; iprovalicarb; benthiavalicarb;cyazofamid, zoxamide, ethaboxam; nicobifen; fenhexamid; quinoxyfen;diethofencarb and acibenzolar S-methyl.

The present invention is further illustrated in detail with productionexamples, formulation examples, test examples and other manner, butshould not be construed to be limited thereto.

At first, the production examples are illustrated as follows.

PRODUCTION EXAMPLE 1

2 g of N-(3-bromopyridine-2-yl)-2,2-dimethylpropionamide, 1.4 g of3,4-dimethoxyphenylboronic acid, 5 g of tripotassium phosphate hydrate,190 mg of {1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium(II)methylenechloride complex and 50 ml of ethyleneglycoldimethylether weremixed, followed by stirring under a nitrogen atmosphere at 80° C. for 2hours. Then, the reaction mixture was added to water to be extractedwith ethyl acetate. The organic layer was concentrated under reducedpressure and then the concentrated residue obtained was subjected to asilica gel column chromatography (eluent; ethylacetate) to obtain 2.1 gof N-(3-(3,4-dimethoxyphenyl)pyridine-2-yl)-2,2-dimethylpropionamide.

¹H-NMR(CDCl₃,TMS)δ(ppm): 1.15(9H,s), 3.89(3H,s), 3.94(3H,s),6.87-6.98(3H,m), 7.17(1H,dd,J=4.8 Hz,7.6 Hz), 7.61(1H,dd,J=2.0 Hz,7.6Hz), 7.69(1H,s), 8.47(1H,dd,J=2.0 Hz,4.8 Hz)

The mixture of 2.1 g ofN-(3-(3,4-dimethoxyphenyl)pyridine-2-yl)-2,2-dimethylpropionamide, 20 mlof methanol and 15 ml of aqueous 3M potassium hydroxide was heated underreflux for 4 hours. After being cooled down to room temperature, thereaction mixture was added with water to be extracted with ethylacetate.The organic layer was concentrated under reduced pressure and then theconcentrated residue was subjected to a silica gel column chromatography(eluent; ethylacetate) to obtain 1.2 g of2-amino-3-(3,4-dimethoxyphenyl)pyridine.

¹H-NMR(CDCl₃,TMS)δ(ppm): 3.90(3H,s), 3.93(3H,s), 4.62(2H,s),6.74(1H,dd,J=4.9 Hz,7.3 Hz), 6.94-7.01(3H,m), 7.36(1H,dd,J=1.7 Hz,7.3Hz), 8.06(1H,dd,J=1.7 Hz,4.9 Hz) 0.5 g of2-(2-propynyloxy)-2-(4-chlorophenyl)acetyl chloride (, which wasprepared by the method of Referencial Production Example 1 describedhereinafter) was added dropwise to the mixture of 0.44 g of2-amino-3-(3,4-dimethoxyphenyl)pyridine, 0.20 g of triethylamine, 0.05 gof 4-dimethylaminopyridine and 15 ml of tetrahydrofuran, followed bystirring at room temperature for 3 hours. Thereafter, the reactionmixture was added with ethylacetate and then filtrated to removeinsolubles. The filtrate was concentrated under reduced pressure andthen the residue was subjected to a silica gel column chromatography(eluent; hexane/ethylacetate=1/1) to obtain 0.31 g ofN-(3-(3,4-dimethoxyphenyl)pyridine-2-yl)-2-(2-propynyloxy)-2-(4-chlorophenyl)acetamide(, which is referred to as the compound of the present invention (IV-1)hereinafter).

¹H-NMR(CDCl₃,TMS)δ(ppm): 2.47(1H,t,J=2.4 Hz), 3.85(3H,s), 3.94(3H,s),4.01(1H,dd,J=2.4 Hz,15.7 Hz), 4.18(1H,dd,J=2.4 Hz,15.7 Hz), 5.05(1H,s),6.84-6.88(3H,m), 7.18(1H,dd,J=4.8 Hz,7.7 Hz), 7.28-7.33(4H,m),7.63(1H,dd,J=1.7 Hz,7.7 Hz), 8.47(1H,dd,J=1.7 Hz,4.8 Hz), 8.79(1H,s)

PRODUCTION EXAMPLE 2

12 g of 4-chloro-3-nitropyridine, 11 g of 3,4-dimethoxyphenylboronicacid, 39 g of tripotassium phosphate hydrate, 988 mg of(1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II)methylenechloride complex and 100 ml of ethyleneglycoldimethylether weremixed, followed by stirring under a nitrogen atmosphere at 80° C. for 2hours. Then, the reaction mixture was added with water to be extractedwith ethylacetate. The organic layer was dried by anhydrous magnesiumsulfate and then concentrated under reduced pressure, followed by theresidue being subjected to a silica gel column chromatography (eluent;hexane/ethylacetate=1/1) to obtain 13 g of4-(3,4-dimethoxyphenyl)-3-nitropyridine.

¹H-NMR(CDCl₃,TMS)δ(ppm): 3.89(3H,s), 3.94(3H,s), 6.83-6.96(3H,m),7.42(1H,d,J=4.8 Hz), 8.76(1H,d,J=4.8 Hz), 9.00(1H,s)

5.0 g of 4-(3,4-dimethoxyphenyl)-3-nitropyridine was added to themixture of 25 ml of acetic acid, 25 ml of water and 4.3 g of iron powderat 70° C., followed by stirring for 2 hours. Then, the reaction mixturewas added with aqueous sodium bicarbonate to be extracted withethylacetate. The organic layer was concentrated under reduced pressureand then the residue was subjected to a silica gel column chromatography(eluent; hexane/ethylacetate=1/1) to obtain 3.2 g of3-amino-4-(3,4-dimethoxyphenyl)pyridine.

¹H-NMR(CDCl₃,TMS)δ(ppm): 3.83(2H,s), 3.91(3H,s) 3.93(3H,s),6.95-7.05(4H,m), 8.05(1H,d,J=4.8 Hz), 8.14(1H,s)

0.4 g of 2-(2-propynyloxy)-2-(4-chlorophenyl)acetyl chloride was addeddropwise to the mixture of 0.40 g of3-amino-4-(3,4-dimethoxyphenyl)pyridine, 0.21 g of triethylamine and 10ml of tetrahydrofuran, followed by stirring at room temperature for 2hours. Then, the reaction mixture was added with ethylacetate and thenfiltrated to remove insolubles. The filtrate was concentrated underreduced pressure and then the residue was subjected to a silica gelcolumn chromatography (eluent; hexane/ethylacetate=1/1) to obtain 0.50 gofN-(4-(3,4-dimethoxyphenyl)pyridine-3-yl)-2-(2-propynyloxy)-2-(4-chlorophenyl)acetamide(, which is referred to as the compound of the present invention (III-1)hereinafter).

¹H-NMR(CDCl₃,TMS)δ(ppm): 2.49(1H,t,J=2.4 Hz), 3.90-3.99(7H,m),4.16(1H,dd,J=2.4 Hz,16.0 Hz), 5.08(1H,s), 6.88(1H,d,J=2.0 Hz),6.95(1H,dd,J=2.0 Hz,8.3 Hz), 7.01(1H,d,J=8.3 Hz), 7.21(1H,d,J=4.8 Hz),7.29(2H,d,J=8.3 Hz), 7.34(2H,d,J=8.3 Hz), 8.42(1H,d,J=4.8 Hz),8.70(1H,s), 9.51(1H,s)

PRODUCTION EXAMPLE 3

8.5 g of N-(3-bromopyridine-4-yl)-2,2-dimethylpropionamide, 5.0 g of3,4-dimethoxyphenylboronic acid, 17.5 g of tripotassium phosphatehydrate, 670 mg of{1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium(II)methylenechloride complex and 100 ml of ethyleneglycoldimethylether weremixed, followed by stirring under a nitrogen atmosphere at 80° C. for 2hours. Then, the reaction mixture was added with water to be extractedwith ethylacetate. The organic layer was concentrated under reducedpressure, followed by the residue being subjected to a silica gel columnchromatography (eluent; ethylacetate) to obtain 8 g ofN-3-(3,4-dimethoxyphenyl)pyridine-4-yl)-2,2-dimethylpropionamide.

¹H-NMR(CDCl₃,TMS)δ(ppm): 1.14(9H,s), 3.91(3H,s), 3.97(3H,s),6.86(1H,d,J=2.0 Hz), 6.93(1H,dd,J=2.0 Hz,8.0 Hz), 7.03(1H,d,J=8.0 Hz),7.81(1H,s), 8.41(1H,s), 8.42(1H,d,J=5.5 Hz), 8.50(1H,d,J=5.5 Hz)

4.0 g ofN-(3-(3,4-dimethoxyphenyl)pyridine-4-yl)-2,2-dimethylpropionamide, 20 mlof methanol and 15 ml of aqueous 3M potassium hydroxide were mixed,followed by for 4 hours heating with reflux. Then, the reaction mixturewas cooled down to room temperature, and then the reaction mixture wasadded with water to be extracted by ethylacetate. The organic layer wasconcentrated under reduced pressure and then the residue was subjectedto a silica gel column chromatography (eluent; hexane/ethylacetate=1/1)to obtain 2.3 g of 4-amino-3-(3,4-dimethoxyphenyl)pyridine.

¹H-NMR(CDCl₃,TMS) (ppm): 3.86(2H,s), 3.93(6H,s), 6.95(1H,d,J=8.3 Hz),7.03-7.05(2H,m), 7.22-7.27(2H,m), 8.11 (1H,d,J=2.8 Hz) 0.4 g of2-(2-propynyloxy)-2-(4-chlorophenyl)acetyl chloride was added dropwiseto the mixture of 0.40 g of 4-amino-3-(3,4-dimethoxyphenyl)pyridine,0.25 g of triethylamine and 10 ml of tetrahydrofuran, followed bystirring at room temperature for 3 hours. Thereafter, the reactionmixture was added with ethylacetate and then fittrated to removeinsolubles. The filtrate was concentrated under reduced pressure andthen the residue was subjected to a silica gel column chromatography(eluent; hexane/ethylacetate=1/1) to obtain 0.72 g ofN-(3-(3,4-dimethoxyphenyl)pyridine-4-yl)-2-(2-propynyloxy)-2-(4-chlorophenyl)acetamide(, which is referred to as the compound of the present invention (II-1)hereinafter).

¹H-NMR(CDCl₃,TMS)δ(ppm): 8.99(1H,s), 8.68-8.71(1H,m), 8.43(1H,dd,J=4.8Hz,1.6 Hz), 7.00-7.37(8H,m), 5.09(1H,s), 3.95-4.20(8H,m),2.47(1H,t,J=2.4 Hz)

PRODUCTION EXAMPLE 4

To 50 ml of ethyleneglycoldimethylether, 4.76 g of2-chloro-3-nitropyridine, 6.00 g of 3,4-dimethoxyphenylboronic acid,19.1 g of tripotassium phosphate hydrate and 490 mg of{1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium(II)methylenechloride complex were added, followed by stirring under anitrogen atmosphere at 80° C. for 4 hours. Thereafter, the reactionmixture was cooled down to room temperature followed by filtration, andthen the filtrate was concentrated under reduced pressure. The residuewas subjected to a silica gel column chromatography to obtain 5.35 g of2-(3,4-dimethoxyphenyl)-3-nitropyridine.

¹H-NMR(CDCl₃,TMS)δ(ppm): 8.83(1H,dd,J=1.2 Hz,4.6 Hz), 8.07(1H,dd,J=1.1Hz,8.3 Hz), 7.39(1H,dd,J=4.6 Hz,8.3 Hz), 7.19(1H,d,J=2.0 Hz),7.12(1H,dd,J=2.0 Hz,8.3 Hz), 6.93(1H,d,J=8.3 Hz), 3.93(6H,s)

2.8 g of 4-(3,4-dimethoxyphenyl)-3-nitropyridine was dissolved to 100 mlof ethanol at room temperature, followed by addition of 150 mg of 5%platinum-carbon and then stirring under a hydrogen atmosphere for 4hours. Thereafter, the reaction mixture was filtrated through celite,followed by the filtrate being concentrated under reduced pressure. Theresidue was subjected to a silica gel column chromatography (eluent;hexane/ethylacetate=1/1) to obtain 2.1 g of3-amino-2-(3,4-dimethoxyphenyl)pyridine.

Melting point: 213.5° C.

0.85 g of 2-(2-propynyloxy)-2-(4-chlorophenyl)acetyl chloride was addeddropwis to the mixture of 0.90 g of3-amino-2-(3,4-dimethoxyphenyl)pyridine, 0.40 g of triethylamine and 15ml of tetrahydrofuran, followed by stirring at room temperature for 2hours. Thereafter, the reaction mixture was added with ethylacetate andthen filtrated to remove insolubles. The filtrate was concentrated underreduced pressure and then the residue was subjected to a silica gelcolumn chromatography (eluent; hexane/ethylacetate=1/1) to obtain 1 g ofN-(2-(3,4-dimethoxyphenyl)pyridine-3-yl)-2-(2-propynyloxy)-2-(4-chlorophenyl)acetamide(, which is referred to as the compound of the present invention (1-1)hereinafter).

Melting point: 125.2° C.

PRODUCTION EXAMPLE 5

40.0 g of 4-bromochlorobenzene was dissolved to 140 ml oftetrahydrofuran under a nitrogen atmosphere and then added with 5.33 gof magnesium, followed by stirring to prepare Grignard reagent. 750 mlof tetrahydrofuran was dissolved with 49.3 g of dimethyl oxalate,followed by dropping at −70° C. with Grignard reagent aforementioned for30 minutes. Thereafter, the reaction mixture was warmed to roomtemperature in 2 hours, followed by stirring at room temperature for 2hours. Then, the reaction mixture was added with ice water and aqueoussaturated ammonium chloride, followed by concentration under reducedpressure. The residue was filtrated, followed by the filtrate beingextracted with ethylacetate. The organic layer was washed by aqueoussaturated sodium chloride and then dried by magnesium sulfate, followedby concentration under reduced pressure. The residue was subjected to asilica gel column chromatography to obtain 22.1 g of4-chlorophenylglyoxylic acid methyl ester.

¹H-NMR(CDCl₃,TMS)δ(ppm):7.98-8.01(2H,m), 7.48-7.51(2H,m), 3.98(3H,s)

To 300 ml of ethanol, 12.2 g of 4-chlorophenylglyoxylic acid methylester and 12.6 g of aqueous 20% sodium hydroxide were added, followed bystirring at room temperature for 3 hours. Thereafter, the reactionmixture was acidified by addition of 36% hydrochloric acid, followed byextraction in three times with chloroform. The organic layer was driedby anhydrous magnesium sulfate and then concentrated under reducedpressure. The residue was washed by hexane and then dried to obtain 5.2g of 4-chlorophenylglyoxylic acid.

¹H-NMR(CDCl₃,TMS)δ(ppm): 8.36-8.39(1H,m), 8.0(1H,br), 7.51-7.54 (2H,m)

To 20 ml of toluene, 1.5 g of 4-chlorophenylglyoxylic acid, 0.95 ml ofthionyl chloride and 20 mg of N,N-dimethylformamide were added, followedby stirring at 80° C. for 1 hour. Thereafter, the reaction mixture wascooled down to room temperature and then concentrated under reducedpressure to obtain crude 4-chlorophenylglyoxyl chloride. To the solutionprepared by mixing 1.0 g of 3-amino-2-chloropyridine, 1.7 ml oftriethylamine and 20 ml of tetrahydrofuran; 4-methylphenylglyoxylchloride described above was added at the temperature range of from 0 to5° C., followed by stirring at room temperature for 2 hours. Thereafter,the reaction mixture was added with water to be extracted withethylacetate. The organic layer obtained was successively washed by 5%hydrochloric acid, aqueous saturated sodium bicarbonate and aqueoussaturated sodium chloride and then dried by magnesium sulfate, followedby concentration under reduced pressure. The residue was washed byhexane to obtain 1.5 g ofN-(2-chloropyridine-3-yl)-2-oxo-2-(4-chlorophenyl)acetamide.

¹H-NMR(CDCl₃,TMS)δ(ppm): 9.59(1H,s), 8.84(1H,dd,J=8.0 Hz,1.6 Hz),8.42(2H,d,J=8.8 Hz), 8.22(dd,1H,J=4.8 Hz,1.6 Hz), 7.52(2H,d,J=8.8 Hz),7.35(dd,1H,J=8.4 Hz,4.7 Hz)

To 10 ml of ethanol, 1.0 g ofN-(2-chloropyridine-3-yl)-2-oxo-2-(4-chlorophenyl)acetamide wasdissolved and was added with 38 mg of sodium borohydride at 0° C.,followed by further stirring at room temperature for 1 hour. Thereafter,the reaction mixture was added with aqueous saturated ammonium chlorideto be extracted with ethylacetate. The organic layer was successivelywashed by aqueous saturated sodium bicarbonate and aqueous saturatedsodium chloride and then dried by magnesium sulfate, followed byconcentration under reduced pressure to obtain 1.0 g ofN-(2-chloropyridine-3-yl)-2-hydroxy-2-(4-chlorophenyl)acetamide.

¹H-NMR(CDCl₃,TMS) (ppm): 9.00(1H,s), 8.71(1H,dd,J=8.0 Hz,1.6 Hz),8.12(dd,1H,J=4.8 Hz,2.0 Hz),7.39-7.49(4H,m),7.24-7.27(1H,m),5.29(1H,d,J=3.6 Hz),3.30(1H,d, J=3.6 Hz)

To 10 ml of ethyleneglycoldimethylether, 0.72 g ofN-(2-chloro-pyridine-3-yl)-2-hydroxy-2-(4-chlorophenyl)acetamide, 1.57 gof 3,4-dimethoxyphenylboronic acid, 1.7 g of tripotassium phosphatehydrate and 63 mg of{1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium(II)methylenechloride complex were mixed, followed by stirring under anitrogen atmosphere at 80° C. for 3 hours. Thereafter, the reactionmixture was cooled down to room temperature and then filtrated, followedby concentrating the filtrate under reduced pressure. The residue wassubjected to a silica gel column chromatography to obtain 0.54 g ofN-{2-(3,4-dimethoxyphenyl)pyridine-3-yl}-2-hydroxy-2-(4-chlorophenyl)acetamide(, which is referred to as the compound of the present invention (1-2)hereinafter).

¹H-NMR(CDCl₃,TMS)δ(ppm): 8.69(1H,dd,J=8.4 Hz,1.2 Hz), 8.45(1H,s),8.36(1H,dd,J=4.4 Hz,1.6 Hz), 7.24-7.33(5H,m), 7.01(1H,s),6.82-6.83(2H,m), 5.03(1H,d,J=2.4 Hz), 4.04(1H,s), 3.95(3H,s), 3.87(3H,s)

To 10 ml of tetrahydrofuran, 0.34 g ofN-{2-(3,4-dimethoxyphenyl)pyridine-3-yl}-2-hydroxy-2-(4-chlorophenyl)acetamideand 0.24 ml of triethylamine were mixed and then further mixed with 0.10ml of methanesulfonyl chloride at about 0° C., followed by stirring atroom temperature for 2 hours. Thereafter, the reaction mixture was addedwith water to be extracted with ethylacetate. The organic layer waswashed by 1% hydrochloric acid and water, and then dried by magnesiumsulfate, followed by concentration under reduced pressure to obtainN-{2-(3,4-dimethoxyphenyl)pyridine-3-yl}-2-methanesulfonyloxy-2-(4-chlorophenyl)acetamide(, which is referred to as the compound of the present invention (1-3)hereinafter). ThisN-{2-(3,4-dimethoxyphenyl)pyridine-3-yl}-2-methanesulfonyloxy-2-(4-chlorophenyl)acetamideand 1.5 ml of 2-propyn-1-ol were mixed, followed by stirring at about80° C. for 3 hours. Thereafter, the reaction mixture was cooled down toroom temperature and then added with water, followed by extraction withethylacetate. The organic layer was successively washed by 3%hydrochloric acid, aqueous saturated sodium bicarbonate and aqueoussaturated sodium chloride, and then dried by magnesium sulfate, followedby concentration under reduced pressure. The residue was subjected to asilica gel column chromatography to obtain 123 mg ofN-{2-(3,4-dimethoxyphenyl)-pyridine-3-yl}-2-(2-propynyloxy)-2-(4-chlorophenyl)acetamide(the compound of the present invention (I-1)).

PRODUCTION EXAMPLE 6

To the mixture of 8 g of aluminum chloride and 80 ml of dichloromethane,7.85 g of ethyloxalyl chloride was added dropwise at 0° C., and further4.60 g of toluene being added dropwise at the same temperature, followedby stirring at room temperature for 1 hour. Thereafter, the reactionmixture was added to ice water to be extracted by chloroform. Theorganic layer was washed twice by aqueous saturated sodium chloride andthen dried by magnesium sulfate followed by concentration under reducedpressure to obtain 9.3 g of 4-methylphenylglyoxylic acid ethyl ester asa crude product.

¹H-NMR(CDCl₃,TMS)δ(ppm): 7.91(2H,d,J=8.2 Hz), 7.31(2H,d,J=8.1 Hz),4.44(2H,q,J=7.1 Hz), 2.44(3H,s), 1.42(2H,t,J=7.0 Hz)

9.3 g of 4-methylphenylglyoxylic acid ethyl ester, 13 ml of aqueous 30%sodium hydroxide and 15 ml of ethanol were mixed, followed by heatingwith reflux for 2 hours. Thereafter, the reaction mixture was cooleddown to room temperature, and then the reaction mixture was acidified byaddition of 5% hydrochloric acid to be extracted by ethylacetate. Theorganic layer was washed twice by aqueous saturated sodium chloride andthen dried by magnesium sulfate, followed by concentration under reducedpressure. The residue was washed by hexane, followed by drying to obtain5.2 g of 4-methylphenylglyoxylic acid.

¹H-NMR(CDCl₃,TMS)δ(ppm): 8.25(2H,d,J=8.3 Hz), 7.32(2H,d,J=8.0 Hz),4.28(1H,br), 2.45(3H,s)

To 150 ml of toluene, 10.0 g of 4-methylphenylglyoxylic acid, 7.2 ml ofthionyl chloride and 0.2 g of N,N-dimethylformamide were mixed, followedby stirring at 80° C. for 1 hour. Thereafter, the reaction mixture wascooled down to room temperature, and then said reaction mixture wasconcentrated under reduced pressure to obtain 12.1 g of4-methylphenylglyoxyl chloride.

To the solution prepared by mixing 2.1 g of 3-amino-2-chloropyridine and2.5 ml of triethylamine to 50 ml of tetrahydrofuran, 3 g of4-methylphenylglyoxyl chloride was mixed at the temperature range offrom 0 to 5° C., followed by stirring at room temperature for 4 hours.Then the reaction mixture was added with water to be extracted withethylacetate.

The organic layer was successively washed by 5% hydrochloric acid,aqueous saturated sodium bicarbonate and aqueous saturated sodiumchloride and then dried by magnesium sulfate, followed by concentrationunder reduced pressure. The residue was washed by hexane to obtain 4.0 gof N-(2-chloropyridine-3-yl)-2-oxo-2-(4-methylphenyl)acetamide.

¹H-NMR(CDCl₃,TMS)δ(ppm): 9.60(1H,s), 8.86(1H,dd,J=8.4, 1.6 Hz),8.35(2H,d,J=8.0 Hz), 8.20(dd,1H,J=4.4,1.2 Hz), 7.32-7.35(3H,m),2.46(3H,s)

To 10 ml of ethanol, 1.5 g ofN-(2-chloropyridine-3-yl)-2-oxo-2-(4-methylphenyl)acetamide wasdissolved and then added with 62 mg of sodium borohydride at 0° C.,followed by stirring at room temperature for 3 hours. Thereafter, thereaction mixture was added with aqueous saturated ammonium chloride tobe extracted by ethylacetate. The organic layer was successively washedby aqueous saturated sodium bicarbonate and aqueous saturated sodiumchloride, and then dried by magnesium sulfate, followed by concentrationunder reduced pressure to obtain 285 mg ofN-(2-chloropyridine-3-yl)-2-hydroxy-2-(4-methylphenyl)acetamide.

¹H-NMR(CDCl₃,TMS)δ(ppm): 8.93(1H,s), 8.73(1H,dd,J=8.4,1.6 Hz),8.11(dd,1H,J=4.4,1.6 Hz), 7.39(2H,d,J=8.0 Hz), 7.22-7.26(3H,m),5.25(1H,d,J=2.0 Hz), 3.18(1H,d, J=2.0 Hz), 2.36(3H,s)

To 20 ml of ethyleneglycoldimethylether, 1.3 g ofN-(2-chloropyridine-3-yl)-2-hydroxy-2-(4-methylphenyl)acetamide, 1.0 gof 3,4-dimethoxyphenylboronic acid, 3.0 g of tripotassium phosphatehydrate and 0.12 g of{1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium(II)methylenechloride complex were mixed, followed by stirring under anitrogen atmosphere at 80° C. for 3 hours. Thereafter, the reactionmixture was cooled down to room temperature to be filtrated, followed byconcentrating the filtrate under reduced pressure. The residue wassubjected to a silica gel column chromatography to obtain 2.4 g ofN-{2-(3,4-dimethoxyphenyl)pyridine-3-yl}-2-hydroxy-2-(4-methylphenyl)acetamide(, which is referred to as the compound of the present invention (1-4)hereinafter).

¹H-NMR(CDCl₃,TMS)δ(ppm): 8.73(1H,d,J=8.0 Hz), 8.40-8.41(1H,m),8.37(1H,s),7.15-8.24(4H,m),7.01(1H,d,J=1.2 Hz), 6.88-6.90(1H,m),6.84(1H,d,J=8.4 Hz), 5.08(1H,d,J=2.8 Hz), 3.96(3H,s), 3.88(3H,s),3.32(1H,d,J=2.8 Hz), 2.37(3H,s)

To 10 ml of tetrahydrofuran, 0.63 g ofN-{2-(3,4-dimethoxyphenyl)pyridine-3-yl}-2-hydroxy-2-(4-methylphenyl)acetamideand 0.3 ml of triethylamine were dissolved and then added with 0.14 mlof methanesulfonyl chloride at about 0° C., followed by stirring at roomtemperature for 30 minutes. Thereafter, the reaction mixture was addedwith water to be extracted by ethylacetate. The organic layer was washedby water and then dried by anhydrous magnesium sulfate, followed byconcentration under reduced pressure to obtainN-{2-(3,4-dimethoxyphenyl)pyridine-3-yl}-2-methanesulfonyloxy-2-(4-methylphenyl)acetamide(, which is referred to as the compound of the present invention (1-5)hereinafter). ThisN-{2-(3,4-dimethoxyphenyl)pyridine-3-yl}-2-methanesulfonyloxy-2-(4-methylphenyl)acetamideand 2.5 ml of 2-propyn-1-ol were mixed, followed by stirring at around80° C. for 1 hour. Thereafter, the reaction mixture was cooled down toroom temperature and then added with water to be extracted byethylacetate. The organic layer was successively washed by water,aqueous saturated ammonium chloride and aqueous saturated sodiumchloride, and then dried by magnesium sulfate, followed by concentrationunder reduced pressure. The residue was subjected to a silica gel columnchromatography to obtain 397 mg ofN-{2-(3,4-dimethoxyphenyl)pyridine-3-yl}-2-propynyloxy-2-(4-methylphenyl)acetamide(, which is referred to as the compound of the present invention (I-6)hereinafter).

¹H-NMR(CDCl₃,TMS) (ppm): 9.00(1H,s),>8.73(1H,dd,J=8.0 Hz,1.6 Hz),8.42(1H,dd,J=4.4 Hz,1.6 Hz),7.00-7.31(8H,m),5.07(1H,s),3.91-4.17(8H,m),2.47(1H,t,J=2.0 Hz),2.34(3H,s)

PRODUCTION EXAMPLE 7

The mixture of 2.00 g ofN-(2-chloropyridine-3-yl)-2-oxo-2-(4-chlorophenyl)acetamide, 20 ml ofethanol, 800 mg of pyridine and 1.13 g of methoxyamine hydrochloric acidsalt were stirred at room temperature for 2 hours. Thereafter, thereaction mixture was concentrated under reduced pressure. The residueobtained was added with water to be extracted by ethylacetate; theextract was washed twice by 5% hydrochloric acid and aqueous saturatedsodium chloride followed by drying with magnesium sulfate and then thesolvent being distilled off under reduced pressure; and the residue waswashed by n-hexane followed by filtration and drying to obtain 1.95 g ofN-(2-chloropyridine-3-yl)-2-methoxyimino-2-(4-chlorophenyl)acetamide.

¹H-NMR(CDCl₃,TMS)δ(ppm): 8.8-8.9(2H,m), 8.19(1H,dd,J=1.7 Hz,4.6 Hz),7.60-7.70(2H,m), 7.30-7.40(2H,m), 4.14 (3H, s)

To 10 ml of ethyleneglycoldimethylether, 0.5 g ofN-(2-chloropyridine-3-yl)-2-methoxyimino-2-(4-chlorophenyl)acetamide,0.31 g of 3,4-dimethoxyphenylboronic acid, 0.65 g of tripotassiumphosphate hydrate and 25 mg of{1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium(II)methylenechloride complex were mixed, followed by stirring under anitrogen atmosphere at 80° C. for 2 hours. Thereafter, the reactionmixture was cooled down to room temperature to be filtrated, followed byconcentration of the filtrate under reduced pressure. The concentratedresidue was subjected to a silica gel column chromatography to obtain0.55 g ofN-{2-(3,4-dimethoxyphenyl)pyridine-3-yl}-2-methoxyimino-2-(4-chlorophenyl)acetamide(, which is referred to as the compound of the present invention (1-7)hereinafter).

¹H-NMR(CDCl₃,TMS)δ(ppm): 8.81(1H,dd,J=8.7 Hz,2.0 Hz), 8.47(1H,dd,J=4.9Hz,1.6 Hz), 8.34(1H,s), 6.92-7.60(m,8H), 3.93(6H,s), 3.87(3H,s)

PRODUCTION EXAMPLE 8

To 50 ml of ethyleneglycoldimethylether, 0.92 g of2-chloro-3-nitropyridine, 0.80 g of 4-methoxyphenylboronic acid, 3.4 gof tripotassium phosphate hydrate, 130 mg of{1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium(II)methylenechloride complex and 1.5 g of celite were added, followed bystirring under a nitrogen atmosphere at 80° C. for 1.5 hours.Thereafter, the reaction mixture was cooled down to room temperature tobe filtrated, followed by concentration of the filtrate under reducedpressure. The residue was subjected to a silica gel columnchromatography to obtain 0.76 g of 2-(4-methoxyphenyl)-3-nitropyridine.

¹H-NMR(CDCl₃,TMS)δ(ppm): 3.86(3H,s), 6.98(2H,d,J=8.7 Hz),7.37(1H,dd,J=4.7 Hz,8.0 Hz), 7.53(2H,d,J=8.7 Hz), 8.08(1H,dd,J=1.4Hz,8.0 Hz), 8.81(1H,dd,J=1.4 Hz,4.7 Hz) 0.76 g of4-(4-methoxyphenyl)-3-nitropyridine was dissolved to 100 ml of ethanolat room temperature and then added with 50 mg of 5% platinum-carbon,followed by stirring under a hydrogen atmosphere for 4 hours.Thereafter, the reaction mixture was filtrated thruogh celite, followedby concentration of the filtrate under reduced pressure. The residue wassubjected to a silica gel column chromatography (eluent;hexane/ethylacetate=1/1) to obtain 0.45 g of3-amino-2-(4-methoxyphenyl)pyridine.

¹H-NMR(CDCl₃,TMS)δ(ppm): 3.81(2H,br), 3.85(3H,s), 6.97-7.04(4H,m),7.61(2H,d,J=8.7 Hz), 8.10(1H,t,J=2.9 Hz)

0.36 g of 2-(4-chlorophenyl)-2-(2-propynyloxy)acetyl chroride was addeddropwise to the mixture of 0.25 g of3-amino-2-(4-methoxyphenyl)pyridine, 0.19 g of triethylamine and 20 mlof tetrahydrofuran, followed by stirring at room temperature for 2hours. Thereafter, the reaction mixture was added with ethylacetate andthen filtrateed to remove insolubles. After the filtrate wasconcentrated under reduced pressure, the residue was subjected to asilica gel column chromatography (eluent; hexane/ethylacetate=1/1) toobtain 0.55 g ofN-(2-(4-methoxyphenyl)pyridine-3-yl)-2-(2-propynyloxy)-2-(4-chlorophenyl)acetamide(, which is referred to as the compound of the present invention (1-8)hereinafter).

¹H-NMR(CDCl₃,TMS)δ(ppm): 2.49(1H,t,J=1.6 Hz), 3.89(3H,s),3.99(1H,dd,J=2.4 Hz,15.8 Hz), 4.18(1H,dd,J=2.4 Hz,15.8 Hz),5.07(1H,s),7.06(2H,d, J=8.7 Hz),7.21-7.26(1H,m), 7.30-7.37(4H,m),7.54(2H,d,J=8.7 Hz), 8.42(1H,dd,J=1.6 Hz,4.7 Hz), 8.64(1H,dd,J=1.6Hz,8.3 Hz), 8.52(1H,s)

PRODUCTION EXAMPLE 9

To 100 ml of ethyleneglycoldimethylether, 6.0 g of2-chloro-3-nitropyridine, 7.9 g of2-methoxy-4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborane-2-yl)phenol, 19.8 gof tripotassium phosphate hydrate and 780 mg of{1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium(II)methylenechloride complex were added, followed by stirring under anitrogen atmosphere at 80° C. for 3 hours. Thereafter, the reactionmixture was cooled down to room temperature to be filtrated, followed byconcentration of the filtrate under reduced pressure. The residue wassubjected to a silica gel column chromatography to obtain 6.38 g of2-(4-hydroxy-3-methoxyphenyl)-3-nitropyridine.

¹H-NMR(CDCl₃,TMS)δ(ppm): 3.93(3H,s), 6.14(1H,s), 6.96(1H,d,J=7.9 Hz),7.05(1H,dd,J=2.0 Hz,7.9 Hz), 7.17 (1H,d,J=2.0 Hz), 7.37(1H,dd,J=4.7Hz,7.9 Hz), 8.05(1H,dd,J=1.6 Hz,7.9 Hz), 8.80(1H,dd,J=1.6 Hz,4.7 Hz)

To 50 ml of N,N-dimethylformamide, 1.50 g of2-(4-hydroxy-3-methoxyphenyl)-3-nitropyridine, 1.0 g of ethyl iodide and0.90 g of potassium carbonate were added, followed by stirring at roomtemperature for 4 hours. The reaction solution was added with water tobe extracted by ethylacetate. The organic layer obtained wasconcentrated under reduced pressure, followed by subjecting the residueobtained to a silica gel column chromatography to obtain 0.90 g of2-(4-ethoxy-3-methoxyphenyl)-3-nitropyridine.

¹H-NMR(CDCl₃,TMS)δ(ppm): 1.49(3H,t,J=7.1 Hz), 3.92(3H,s),4.15(2H,q,J=7.1 Hz), 6.91(1H,d,J=8.3 Hz), 7.09(1H,dd,J=2.0 Hz,8.3 Hz),7.18(1H,d,J=2.0 Hz), 7.37(1H,dd,J=4.7 Hz,7.9 Hz), 8.05(1H,dd,J=1.6Hz,7.9 Hz), 8.81(1H,dd,J=1.6 Hz,4.7 Hz)

To 100 ml of ethanol, 0.90 g of2-(4-ethoxy-3-methoxyphenyl)-3-nitropyridine and 50 mg of 5%platinum-carbon were added, followed by stirring under a hydrogenatmosphere for 4 hours. Thereafter, the reaction mixture was filtratedthrough celite, followed by concentration of the filtrate under reducedpressure. The residue was subjected to a silica gel columnchromatography (eluent; hexane/ethylacetate=1/1) to obtain 0.72 g of3-amino-2-(4-ethoxy-3-methoxyphenyl)pyridine.

¹H-NMR(CDCl₃,TMS)δ(ppm): 1.48(3H,t,J=6.8 Hz), 3.88(2H,s), 3.91(3H,s),4.14(2H,q,J=6.8 Hz), 6.94(1H,d,J=8.8 Hz), 7.03(2H,d,J=2.8 Hz),7.19-7.25(2H,m), 8.10(1H,t,J=2.8 Hz)

The mixture of 0.20 g of 3-amino-2-(4-ethoxy-3-methoxyphenyl)pyridine,0.15 g of triethylamine and 10 ml of tetrahydrofuran was added dropwisewith 0.30 g of 2-(4-chlorophenyl)-2-(2-propynyloxy)acetyl chloride,followed by stirring at room temperature for 2 hours. Thereafter, thereaction mixture was added with ethylacetate and then filtrated toremove insolubles. After the filtrate being concentrated under reducedpressure, the residue was subjected to a silica gel columnchromatography (eluent; hexane/ethylacetate=1/1) to obtain 0.30 g ofN-(2-(4-ethoxy-3-methoxyphenyl)pyridine-3-yl)-2-(2-propynyloxy)-2-(4-chlorophenyl)acetamide(, which is referred to as the compound of the present invention (1-9)hereinafter).

¹H-NMR(CDCl₃,TMS)_(b)(ppm): 1.52(3H,t,J=7.1 Hz), 2.49(1H,t,J=2.4 Hz),3.94(3H,s), 3.97(1H,dd,J=2.4 Hz,15.8 Hz), 4.18(1H,dd,J=2.4 Hz,15.8 Hz),4.19(2H,q,J=7.1 Hz), 5.08(1H,s), 7.01(1H,d,J=7.9 Hz), 7.11-7.15(2H,m),7.24(1H,dd,J=4.7 Hz,7.9 Hz), 7.31(2H,d,J=8.7 Hz), 7.35(2H,d,J=8.7 Hz),8.42(1H,dd,J=1.6 Hz,4.7 Hz), 8.68(1H,dd,J=1.6 Hz,7.9 Hz), 8.96(1H,s)

PRODUCTION EXAMPLE 10

To 100 ml of N,N-dimethylformamide, 3.0 g of2-(4-hydroxy-3-methoxyphenyl)-3-nitropyridine, 1.5 g of3-bromo-1-propyne and 1.7 g of potassium carbonate were added, followedby stirring at room temperature for 4 hours. The reaction solution wasadded with dilute hydrochloric acid to be extracted by ethylacetate. Theorganic layer was concentrated under reduced pressure, followed bysubjecting the residue obtained to a silica gel column chromatography toobtain 1.8 g of 2-(3-methoxy-4-(2-propynyloxy)phenyl)-3-nitropyridine.

¹H-NMR(CDCl₃,TMS)_(b)(ppm): 2.54(1H,t,J=2.4 Hz), 3.92(3H,s),4.81(2H,d,J=2.4 Hz), 7.07-7.13(2H,m), 7.20(1H,d,J=1.6 Hz),7.39(1H,dd,J=4.7 Hz,8.3 Hz), 8.07(1H,dd,J=1.6 Hz,8.3 Hz),8.82(1H,dd,J=1.6 Hz,4.7 Hz)

The mixture of 5 ml of acetic acid, 30 ml of water and 1.3 g of ironpowder was heated to 75° C. and then added dropwise with 1.6 g ofsolution of 2-(3-methoxy-4-(2-propynyloxy)phenyl)-3-nitropyridinedissolved in 10 ml of ethylacetate. After being heated with reflux for 3hours, the reaction solution was added with aqueous sodium bicarbonateto be extracted by ethylacetate. The organic layer was dried bymagnesium sulfate followed by concentration under reduced pressure; andthen the residue was subjected to a silica gel column chromatography toobtain 1.4 g of 3-amino-2-(3-methoxy-4-(2-propynyloxy)phenyl)pyridine.

¹H-NMR(CDCl₃,TMS)δ(ppm): 2.52(1H,t,J=2.4 Hz), 3.89(2H,s), 3.91(3H,s),4.80(2H,d,J=2.4 Hz), 7.02-7.05(2H,m), 7.10(1H,d,J=8.8 Hz),7.22-7.26(2H,m), 8.10(1H,ddd,J=0.4 Hz,2.4 Hz,3.6 Hz)

0.25 g of 2-(4-chlorophenyl)-2-(2-propynyloxy)acetyl chloride was addeddropwise to the mixture of 0.20 g of3-amino-2-(3-methoxy-4-(2-propynyloxy)phenyl)pyridine, 0.15 g oftriethylamine and 10 ml of tetrahydrofuran, followed by stirring at roomtemperature for 2 hours. Thereafter, the reaction mixture was added withethylacetate and then filtrated to remove insolubles. After the filtratewas concentrated under reduced pressure, the concentrated residue wassubjected to a silica gel column chromatography (eluent;hexane/ethylacetate=1/1) to obtain 0.30 g ofN-(2-(3-methoxy-4-(2-propynyloxy)phenyl)pyridine-3-yl)-2-(2-propynyloxy)-2-(4-chlorophenyl)acetamide(, which is referred to as the compound of the present invention (1-10)hereinafter).

¹H-NMR(CDCl₃,TMS)₆(ppm): 2.51(1H,t,J=2.4 Hz), 2.55(1H,t,J=2.4Hz), >3.94(3H,s), 3.97(1H,dd,J=2.4 Hz,16.2 Hz), 4.18(1H,dd,J=2.4 Hz,16.2Hz), 4.86(2H,d,J=2.4 Hz), 5.08(1H,s), 7.12-7.20(3H,m), 7.25(1H,dd,J=4.7Hz,7.9 Hz), 7.31(2H,d,J=8.3 Hz), 7.35(2H,d,J=8.3 Hz), 8.42(1H,dd,J=1.6Hz,4.7 Hz), 8.68(1H,dd,J=1.6 Hz,7.9 Hz), 8.95(1H,s)

PRODUCTION EXAMPLE 11

10 g of 4-chlorophenylglyoxylic acid methyl ester was dissolved to 100ml of acetonitrile and then added with 40 g of triphenylphosphine and 23g of carbon tetrachloride, followed by stirring at room temperature for4 hours. The reaction solution was concentrated to subject the residueto a silica gel column chromatography (eluent; hexane/ethylacetate=10/1)to obtain 13.7 g of 2-(chlorophenyl)-3,3-dichloroacrylic acid methylester.

¹H-NMR(CDCl₃,TMS)δ(ppm): 3.79(3H,s), 7.30(2H,d,J=8.3 Hz),7.37(2H,d,J=8.3 Hz) 13.5 g of 2-(chlorophenyl)-3,3-dichloroacrylic acidmethyl ester was dissolved to 130 ml of methanol and then added dropwisewith aqueous potassium hydroxide (4.0 g of potassium hydroxide, 70 ml ofwater). After being stirred at room temperature for 8 hours, thereaction solution was semi-concentrated, followed by addition of dilutehydrochloric acid to be extracted by ethylacetate. The organic layer wasdried by magnesium sulfate, followed by concentration under reducedpressure. The crystal obtained was washed by hexane to obtain 9.0 g of2-(chlorophenyl)-3,3-dichloroacrylic acid.

¹H-NMR(CDCl₃,TMS)δ(ppm): 7.28(2H,dd,J=1.6 Hz,8.3 Hz), 7.38(2H,dd,J=1.6Hz,8.3 Hz), 10.25(1H,br)

0.63 g of 2-(chlorophenyl)-3,3-dichloroacrylic acid and 0.36 g ofthionyl chloride were added to 10 ml of toluene, followed by beingheated under stirring for 2 hours. The reaction solution wasconcentrated under reduced pressure to obtain a crude2-(chlorophenyl)-3,3-dichloroacryl chloride. The crude2-(chlorophenyl)-3,3-dichloroacryl chloride obtained was added dropwiseto 10 ml of tetrahydrofuran solution containing of 0.50 g oftriethylamine and 0.30 g of 3-amino-2-(3,4-dimethoxyphenyl)pyridine,followed by stirring at room temperature for 3 hours; and then thereaction solution was added with ethylacetate and then filtrated toremove insolubles. The filtrate was concentrate under reduced pressure,followed by subjecting the residue to a silica gel column chromatographyto obtain 60 mg ofN-(2-(3,4-dimethoxyphenyl)-pyridine-3-yl)-2-(chlorophenyl)-3,3-dichloroacrylamide.

¹H-NMR(CDCl₃,TMS)δ(ppm): 3.83(3H,s), 3.95(3H,s), 6.65-6.70(2H,m),6.93(1H,s),7.23-7.31(3H,m),7.37(2H,d,J=7.6 Hz), 7.49(1H,s),8.41(1H,d,J=4.8 Hz), 8.72(1H,d,J=8.4 Hz)

PRODUCTION EXAMPLE 12

To 10 ml of toluene, 0.19 g of -2-(4-chlorophenyl)-2-methoxyacetic acidand 0.14 g of thionyl chloride were added, followed by being heatedunder stirring for 2 hours. The reaction solution was concentrated underreduced pressure to obtain a crude 2-(chlorophenyl)-2-methoxyacetylchloride. The crude 2-(chlorophenyl)-2-methoxyacetyl chloride obtainedwas added dropwise at 0° C. to 10 ml of tetrahydrofuran solutioncontaining 0.11 g of triethylamine and 0.22 g of3-amino-2-(3,4-dimethoxyphenyl)pyridine. After being stirred at roomtemperature for 3 hours, the reaction solution was concentrated underreduced pressure, followed by subjecting the residue to a silica gelcolumn chromatography to obtain 127 mg ofN-(2-(3,4-dimethoxyphenyl)-pyridine-3-yl)-2-(4-chlorophenyl)-2-methoxyacetamide.

¹H-NMR(CDCl₃,TMS)δ(ppm): 3.31(3H,s), >3.95(3H,s), 3.98(3H,s),4.67(1H,s), 7.00(1H,d,J=8.0 Hz), 7.10-7.16(2H,m), 7.24(1H,dd,J=4.8Hz,8.4 Hz), 7.30(2H,d,J=8.4 Hz), 7.35(2H,d,J=8.4 Hz), 8.42(1H,dd,J=1.6Hz,4.8 Hz), 8.67(1H,dd,J=1.6 Hz,8.4 Hz), 8.95(1H,s)

Next, the illustrated below is a referential production exampleproducing a production intermediate for the compound of the presentinvention.

REFERENTIAL PRODUCTION EXAMPLE 1

80.2 g of 4-chlorophenylglyoxylic acid methyl ester was dissolved to 500ml of methanol and then added with 3.8 g of sodium borohydride at thetemperature range of from 0 to 5° C., followed by stirring at roomtemperature for 2 hours. Thereafter, the reaction mixture wasconcentrated under reduced pressure, followed by addition of water tothe residue to be extracted by ethylacetate. The organic layer wasconcentrated under reduced pressure, followed by subjecting theconcentrated residue to a silica gel column chromatography (eluent;hexane/ethylacetate=5/1 to 2/1) to obtain 62.4 g of2-hydroxy-2-(4-chlorophenyl)acetic acid methyl ester.

¹H-NMR(CDCl₃,TMS)δ(ppm): 3.51(1H,d,J=5.3 Hz), 3.76(3H,S),5.15(1H,d,J=5.3 Hz), 7.31-7.38(4H,m)

To 200 ml of tetrahydrofuran, 62.4 g of2-hydroxy-2-(4-chlorophenyl)acetic acid methyl ester and 40.8 g oftriethylamine were dissolved and then added with 42.8 g ofmethanesulfonyl chloride at 0° C., followed by stirring at roomtemperature for 3 hours. Thereafter, the reaction mixture wasconcentrated under reduced pressure, followed by addition ofethylacetate to the residue and then filtrated to remove solid material.After the filtrate being concentrated under reduced pressure, theresidue was subjected to a silica gel column chromatography (eluent;hexane/ethylacetate=3/1) to obtain 75.6 g of2-methanesulfonyloxy-2-(4-chlorophenyl)acetic acid methyl ester.

¹H-NMR(CDCl₃,TMS)δ(ppm): 3.12(3H,s), 3.78(3H,s), 5.92(1H,s),7.36-7.43(4H,m) 70 g of 2-methanesulfonyloxy-2-(4-chlorophenyl) aceticacid methyl ester was mixed with 70 g of 2-propynylalcohol, followed bystirring at 80° C. for 1.5 hours. Thereafter, the reaction mixture wasadded with toluene followed by concentration under reduced pressure. Theconcentrated residue was subjected to a silica gel column chromatography(eluent; hexane/ethylacetate=10/1) to obtain 64.6 g of a mixture of2-(2-propynyloxy)-2-(4-chlorophenyl)acetic acid methyl ester and2-(2-propynyloxy)-2-(4-chlorophenyl)acetic acid (2-propynyl).(2-propynyloxy)-2-(4-chlorophenyl)acetic acid (2-propynyl)

¹H-NMR(CDCl₃,TMS)δ(ppm): 2.47(1H,t,J=2.4 Hz), 2.51(1H,t,J=2.4 Hz),4.18(2H,dd,J=2.4 Hz,16.2 Hz), 4.31(2H,dd,J=2.4 Hz,16.2 Hz),4.67(2H,dd,J=2.4 Hz,15.4 Hz), 4.76(2H,dd,J=2.4 Hz,15.4 Hz), 5.23(1H,s),7.33-7.42(4H,m) 2-(2-propynyloxy)-2-(4-chlorophenyl)acetic acid methylester

¹H-NMR(CDCl₃,TMS)δ(ppm): 2.50(1H,t,J=2.4 Hz), 3.12(3H,s),4.16(2H,dd,J=2.4 Hz,16.2 Hz), 4.30(2H,dd,J=2.4 Hz,16.2 Hz), 5.19(1H,s),7.33-7.42(4H,m)

64.6 g of the mixture of (2-(2-propynyloxy)-2-(4-chlorophenyl)aceticacid methyl ester and 2-(2-propynyloxy)-2-(4-chlorophenyl) acetic acid(2-propynyl), which mentioned above, were dissolved to 800 ml oftetrahydrofuran and then added dropwise at 0° C. with aqueous lithiumhydroxide (a mixture of 6.74 g of lithium hydroxide and 280 ml ofwater). After being stirred in the range of from 0° C. to roomtemperature for 3 hours, the reaction solution was added with dilutehydrochloric acid to be extracted by ethylacetate. The organic layer wasdried by anhydrous magnesium sulfate, followed by concentration underreduced pressure. The crystal produced was washed by hexane to obtain43.4 g of 2-(2-propynyloxy)-2-(4-chlorophenyl) acetic acid (Intermediate5-003).

¹H-NMR(CDCl₃,TMS)δ(ppm): 2.51(1H,t,J=2.4 Hz), 4.15(1H,dd,J=2.4 Hz,16.0Hz), 4.32(1H,dd,J=2.4 Hz,16.0 Hz), 7.33-7.44(4H,m), 8.70-9.50(1H,br)

4.7 g of 2-(2-propynyloxy)-2-(4-chlorophenyl)acetic acid and 3.0 g ofthionyl chloride were dissolved to 50 ml of toluene, followed bystirring at 100° C. for 2 hours. The reaction solution was concentratedunder reduced pressure to obtain 5.0 g of2-(2-propynyloxy)-2-(4-chlorophenyl)acetic acid chloride.

¹H-NMR(CDCl₃,TMS)δ(ppm): 2.57(1H,t,J=2.0 Hz), 4.28(1H,dd,J=2.0 Hz,16.2Hz), 4.36(1H,dd,J=2.0 Hz,16.2 Hz), 5.39(1H,s), 7.37-7.44(4H,m)

Next formulation examples are shown. Parts represent parts by weight.

FORMULATION EXAMPLE 1

Fifty parts of each of the compounds of the present invention (I-1) to(I-12), (II-1), (III-1) and (IV-1), 3 parts of calcium ligninsulfonate,2 parts of magnesium laurylsulfate and 45 parts of synthetic hydratedsilica are pulverized and mixed well to give wettable powders of eachcompound.

FORMULATION EXAMPLE 2

Twenty parts of each of the compounds of the present invention (I-1) to(I-12), (II-1), (III-1) and (IV-1) and 1.5 parts of sorbitan trioleateare mixed with 28.5 parts of an aqueous solution containing 2 parts ofpolyvinyl alcohol, and wet-pulverized finely. To the obtained mixture,40 parts of an aqueous solution containing 0.05 part of xanthan gum and0.1 part of aluminium magnesium silicate is added and further 10 partsof propylene glycol are added to give a flowable of each compound.

FORMULATION EXAMPLE 3

Two parts of each of the compounds of the present invention (I-1) to(I-12), (II-1), (III-1) and (IV-1), 88 parts of kaolin clay and 10 partsof talc are pulverized and mixed well to give dusts of each compound.

FORMULATION EXAMPLE 4

Five parts of each of the compounds of the present invention (I-1) to(I-12), (II-1), (III-1) and (IV-1), 14 parts of polyoxyethylenestyrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts ofxylene are mixed well to give emulsifiable concentrates of eachcompound.

FORMULATION EXAMPLE 5

Two parts of each of the compounds of the present invention (I-1) to(I-12), (II-1), (III-1) and (IV-1), 1 part of synthetic hydrated silica,2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 partsof kaolin clay are pulverized and mixed well, and water is added theretoand kneeded, granulated and dried to give granules of each compound.

FORMULATION EXAMPLE 6

Ten parts of each of the compounds of the present invention (I-1) to(I-12), (II-1), (III-1) and (IV-1), 35 parts of white carbon containing50% by weight of ammonium polyoxyethylenealkyl ether sulfate and 55parts of water are mixed and wet pulverized finely to give a flowable ofeach compound.

Next, it is shown that the compound of the present invention are usefulfor controlling plant diseases.

Additionally, the control effect was evaluated by visually observing thearea of a lesion on a sample plant in investigation and comparing thearea of a lesion on a non-treatment plant and the area of a lesion on atreated plant with the compound of the present invention.

TEST EXAMPLE 1

Sand loam was compacted in a plastic pot, and a tomato (variety:Ponterosa) was seeded and grown in a green house for 20 days. Thecompounds of the present invention (I-1), (I-2), (I-4), (I-6) to (I-10),(I-12), (II-1), (III-1) and (IV-1) were formulated to flowable accordingto Formulation Example 6, then, diluted with water to provide givenconcentration of 500 ppm, and these diluted solutions were sprayed ontostems and leaves so as to give sufficient adhesion on the surface of thetomato leaves. After spraying, the liquid on the stem was air-dried, anda suspension of zoosporangiua of Phytophthora infestans (about 10,000zoosporangiua were contained in 1 ml of the suspension) was inoculatedby spraying. The amount of the sprayed suspension was about 2 ml for oneplent. After inoculation, the plant was first grown for one day at 23°C. under 90% or more humidity, then further grown for 4 days in thegreen house, which was 24° C. in daytime and 20° C. in night-time.

Then, the areas of a lesion of the plants were obserbed. The lesionareas on the plants treated with the compounds of the present invention(I-1), (I-2), (I-4), (I-6) to (I-10), (I-12), (II-1), (III-1) and (IV-1)were not more than 10% of the lesion area on a non-treatment plant.

TEST EXAMPLE 2

Sand loam was compacted in a plastic pot, and a tomato (variety:Ponterosa) was seeded and grown in a green house for 20 days. Thecompounds of the present invention (1-11) was formulated to flowableaccording to Formulation Example 6, then, diluted with water to providegiven concentration of 200 ppm, and this diluted solution was sprayedonto stems and leaves so as to give sufficient adhesion on the surfaceof the tomato leaves. After spraying, the liquid on the stem wasair-dried, and a suspension of zoosporangiua of Phytophthora infestans(about 10,000 zoosporangiua were contained in 1 ml of the suspension)was inoculated by spraying. The amount of the sprayed suspension wasabout 2 ml for one plent. After inoculation, the plant was first grownfor one day at 23° C. under 90% or more humidity, then further grown for4 days in the green house, which was 24° C. in daytime and 20° C. innight-time.

Then, the areas of a lesion of the plants were obserbed. The lesionareas on the plants treated with the compounds of the present invention(I-11) was not more than 10% of the lesion area on a non-treatmentplant.

Test Example 3

Sand loam was compacted in a plastic pot, and a grape (variety: Berry A)was seeded and grown in a green house for 40 days. The compounds of thepresent invention (I-1), (I-2), (I-6) to (I-12), (II-1), (III-1) and(IV-1) were formulated to flowable according to Formulation Example 6,then, diluted with water to provide given concentration of 200 ppm, andthese diluted solutions were sprayed onto stems and leaves so as to givesufficient adhesion on the surface of grape leaves. After spraying, theliquid on the stem was air-dried, and a suspension of zoosporangiua ofPlasmopara viticola (about 10,000 zoosporangiua were contained in 1 mlof the suspension) was inoculated by spraying. The amount of the sprayedsuspension was about 2 ml for one plant. After inoculation, the plantwas first grown for one day at 23° C. under 90% or more humidity, thenfurther grown for 6 days in the green house, which was 24° C. in daytimeand 20° C. in night-time.

Then, the areas of a lesion of the plants were obserbed. The lesionareas on the plants treated with the present compound (I-1), (I-2),(I-6) to (I-12), (II-1), (III-1) and (IV-1) were not more than 10% ofthe lesion area on a non-treatment plant.

TEST EXAMPLE 4

Sand loam was compacted in a plastic pot, and a grape (variety: Berry A)was seeded and grown in a green house for 40 days. The compounds of thepresent invention (1-4) was formulated to flowable according toFormulation Example 6, then, diluted with water to provide givenconcentration of 200 ppm, and this diluted solution was sprayed ontostems and leaves so as to give sufficient adhesion on the surface ofgrape leaves. After spraying, the liquid on the stem was air-dried, anda suspension of zoosporangiua of Plasmopara viticola (about 10,000zoosporangiua were contained in 1 ml of the suspension) was inoculatedby spraying. The amount of the sprayed suspension was about 2 ml for oneplant. After inoculation, the plant was first grown for one day at 23°C. under 90% or more humidity, then further grown for 6 days in thegreen house, which was 24° C. in daytime and 20° C. in night-time.

Then, the areas of a lesion of the plants were obserbed. The lesionareas on the plants treated with the present compound (I-4) was not morethan 10% of the lesion area on a non-treatment plant.

INDUSTRIAL APPLICABILITY

The compound of the present invention has an excellent controllingactivity against plant diseases and is useful as an active ingredientfor the agent controlling plant diseases.

1. A phenylpyridine compound represented by the formula (1):

[, wherein, in the formula, R¹, R², R³, R⁴ and R⁵ independentlyrepresent a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C1-C6haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, aC2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group, aC1-C6 haloalkoxy group, a C3-C6 alkenyloxy group, a C3-C6 haloalkenyloxygroup, a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group, a C1-C6alkylthio group, a C1-C6 haloalkylthio group, a C3-C6 cycloalkyl group,a C3-C6 cycloalkoxy group or a cyano group; both of R² and R³ may becombined to represent a trimethylene, a tetramethylene or —CH═CH—CH═CH—;R⁶ represents a hydrogen atom or a C1-C3 alkyl group; R⁷, R⁸ and R¹¹independently represent a hydrogen atom, a halogen atom or a C1-C3 alkylgroup; R⁹ and R¹⁰ independently represent a hydroxyl group, a halogenatom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenylgroup, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6haloalkynyl group, a C2-C6 cyanoalkyl group, a C1-C6 alkoxy group, aC1-C6 haloalkoxy group, a C3-C6 alkenyloxy group, a C3-C6 haloalkenyloxygroup, a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group, a C2-C6cyanoalkyloxy group, a C1-C6 alkylthio group, a C1-C6 haloalkylthiogroup, a C3-C6 cycloalkyl group, a C3-C6 cycloalkoxy group, a nitrogroup, a benzyl group or a cyano group; W¹—W²═W³—W⁴ representsN—CR²¹═CR²²—CR²³, CR²⁴—N═CR²⁵—CR²⁶, CR²⁷—CR²⁸═N—CR²⁹ or CR³⁰—CR³¹═CR³²—N{in which R²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷, R²⁸, R²⁹, R³⁰, R³¹ and R³²independently represent a hydrogen atom, a halogen atom, a C1-C3 alkylgroup, a C1-C3 alkoxy group or a C1-C3 haloalkyl group}; X represents anoxygen atom or a sulfur atom; Q represents a group illustrated by thefollowing formulas of Q1 or Q2

{in which R¹⁴ represents a hydrogen atom or a C1-C3 alkyl group, R¹⁵represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkylgroup, a C3-C6 alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynylgroup, a C3-C6 haloalkynyl group, a C3-C6 cycloalkyl group, a (C1-C6alkyl)carbonyl group, a (C1-C6 haloalkyl)carbonyl group, a (C1-C6alkoxy)carbonyl group, a (C1-C6 haloalkoxy)carbonyl group, a (C3-C6alkenyloxy)carbonyl group, a (C3-C6 haloalkenyloxy)carbonyl group, a(C3-C6 alkynyloxy)carbonyl group, a (C3-C6 haloalkynyloxy)carbonyl groupor a C1-C3 alkylsulfonyl group, Z¹ represents an oxygen atom or a sulfuratom, Z² represents an oxygen atom, NOR¹⁶ (in which R¹⁶ represents ahydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynyl group, a C3-C6haloalkynyl group or a C3-C6 cycloalkyl group), CR¹⁷R¹⁸ (in which R¹⁷represents a halogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group,a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C6 alkenyloxygroup, a C3-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group, a C3-C6haloalkynyloxy group or a C3-C6 cycloalkyloxy group and R¹⁸ represents ahydrogen atom, a halogen atom, a C1-C6 alkyl group or a C1-C6 haloalkylgroup) or NNR¹⁹R²⁰ (in which R¹⁹ and R²⁰ independently represent ahydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynyl group or aC3-C6 cycloalkyl group)}].
 2. The phenylpyridine compound according toclaim 1, wherein X is an oxygen atom.
 3. The phenylpyridine compoundaccording to any one of claim 1 or 2, wherein R⁶ is a hydrogen atom. 4.The phenylpyridine compound according to any one of claim 1 to 3 claim1, wherein Q is Q1, R¹⁴ is a hydrogen atom and Z¹ is an oxygen atom. 5.The phenylpyridine compound according to claim 4, wherein R¹⁵ is ahydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6alkenyl group, a C3-C6 haloalkenyl group, a C3-C6 alkynyl group, a C3-C6haloalkynyl group or a C3-C6 cycloalkyl group.
 6. The phenylpyridinecompound according to any one of claim 1 to 3 claim 1, wherein Q is Q2and Z² is NOR¹⁶ (in which R¹⁶ is a hydrogen atom, a C1-C6 alkyl group, aC1-C6 haloalkyl group, a C3-C6 alkenyl group, a C3-C6 haloalkenyl group,a C3-C6 alkynyl group, a C3-C6 haloalkynyl group or a C3-C6 cycloalkylgroup).
 7. The phenylpyridine compound according to claim 1, wherein R¹,R⁴ and R⁵ are hydrogen atoms.
 8. The phenylpyridine compound accordingto any one of claim 1 to 6 claim 1, wherein R¹, R⁴ and R⁵ are hydrogenatoms and R² is a hydrogen atom, a halogen atom, a C1-C6 alkyl group, aC2-C6 alkenyl group, a C3-C6 alkynyl group, a C1-C6 alkoxy group, aC3-C6 alkenyloxy group, a C3-C6 alkynyloxy group, a C1-C6 alkylthiogroup, a C3-C6 cycloalkyl group, a C3-C6 cycloalkoxy group or a cyanogroup.
 9. The phenylpyridine compound according to claim 1, wherein R¹,R², R⁴ and R⁵ are hydrogen atoms.
 10. The phenylpyridine compoundaccording to claim 1, wherein each of R⁹ and R¹⁰ is a C1-C6 alkoxygroup, a C1-C6 haloalkoxy group, a C3C6 alkenyloxy group, a C3-C6haloalkenyloxy group, a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxygroup, a C2-C6 cyanoalkyloxy group or a C3-C6 cycloalkoxy group.
 11. Thephenylpyridine compound according to claim 1, wherein each of R⁹ and R¹⁰is a C1-C4 alkoxy group.
 12. The phenylpyridine compound according toclaim 1, wherein R⁹ and R¹⁰ are methoxy groups.
 13. The phenylpyridinecompound according to claim 1, wherein R⁷, R⁸ and R¹¹ are hydrogenatoms.
 14. The phenylpyridine compound according to any one of claim 1to 13 claim 1, wherein W¹—W²═W³—W⁴ is N—CH═CH—CH, CH—N═CH—CH, CH—CH═N—CHor CH—CH═CH—N.
 15. A fungicidal composition comprising thephenylpyridine compound according to claim 1 and a carrier.
 16. A methodfor controlling plant diseases comprising applying of the phenylpyridinecompound according to claim 1 for plants or soils.